Metal Catalysed Carbon-Carbon Bond-Forming Reactions, Volume 3

, by Roberts, Stanley M.; Xiao, Jianliang; Whittall, John; Pickett, Tom E.

Note: Supplemental materials are not guaranteed with Rental or Used book purchases.

ISBN: 9780470861998 | 0470861991
Cover: Hardcover
Copyright: 11/30/2004

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The chemist has a vast range of high-tech catalysts to use when working in fine chemical synthesis but the catalysts are generally hard to use and require both time, skill and experience to handle properly. The Catalysts for Fine Chemical Synthesis series contains tested and validated procedures which provide a unique range resources for chemists who work in organic chemistry."... of great value to synthetic organic chemists..." (The Chemists, Summer 2003)Volume 3 in the series focuses on catalysts for carbon-carbon bond formation and presents practical and detailed protocols on how to use sophisticated catalysts by the "inventors" and "developers" who created them. The combination of protocols and review commentaries helps the reader to easily and quickly understand and use the new high-tech catalysts.

Series Preface

xvii

Preface to Volume 3

xix

Abbreviations

xxi

List of Chemical Names Used

xxiii

1 Considerations of Industrial Fine Chemical Synthesis

(12)

Mark W. Hooper

(12)

1.1 Introduction

1.2 Types of processes - flow charts

(1)

1.2.1 Classical process

(1)

1.2.2 General catalytic process

(1)

1.3 Costs associated with use of catalysts

(9)

1.3.1 Catalyst fabrication costs

(3)

1.3.2 Intellectual property right (IPR) issues

(1)

1.3.3 Separation costs

(1)

1.3.4 Pre-reaction/immobilisation

(1)

1.3.5 Post reaction - separation

(1)

1.3.6 Industrial examples

(3)

References

(1)

2 Alkylation and Allylation Adjacent to a Carbonyl Group

(22)

2.1 The RuH2(CO)(PPh3)3-catalysed alkylation, alkenylation and arylation of aromatic ketones via carbon-hydrogen bond cleavage

Fumitoshi Kakiuchi, Satoshi Ueno and Naoto Chatani

(7)

2.1.1 Preparation of carbonyldihydrotris(triphenylphosphine) ruthenium

(2)

2.1.2 Synthesis of 8-(2-triethoxysilanylethyl)-3,4-dihydro-2H-naphthalen-1-one

(1)

2.1.3 Synthesis of 8-(1-methyl-2-trimethylsilanylvinyl)-3,4-dihydro-2H-naphthalen-1-one

(1)

2.1.4 Synthesis of 1-biphenyl-2-yl-2,2-dimethylpropan-1-one

(1)

2.1.5 Conclusion

(2)

References

(1)

2.2 Catalytic, asymmetric synthesis of α,α-disubstituted amino acids using a chiral copper-salen complex as a phase transfer catalyst

Michael North and Jose A. Fuentes

(6)

2.2.1 Synthesis of (chsalen)

(1)

2.2.2 Synthesis of copper(II) (chsalen)

(1)

2.2.3 Alkylation of alanine methyl ester Schiff base by chiral salen-metal catalysts, α-benzyl-alanine methyl ester

(2)

2.2.4 Conclusion

(1)

References

(1)

2.3 Asymmetric phase-transfer catalysed alkylation of glycine imines using cinchona alkaloid derived quaternary ammonium salts

Barry Lygo and Benjamin I. Andrews

(9)

2.3.1 Synthesis of (1S,2S,4S,5R,1'R)-1-(anthracen-9-ylmethyl)-5-ethyl-2-[hydroxy(quinolin-4-yl)methyl]-1-azoniabicyclo[2.2.2]octane bromide

(1)

2.3.2 Synthesis of (1S,2S,4S,5R,1'R)-1-(anthracen-9-ylmethyl)-5-ethyl-2-[benzyloxy(quinolin-4-yl)methyl]-1-azoniabicyclo[2.2.2]octane bromide

(2)

2.3.3 Synthesis of (2S)-tert-butyl 2-amino-4-bromopent-4-enoate

(1)

2.3.4 Conclusion

(1)

References

(2)

3 Asymmetric Alkylation or Amination of Allylic Esters

(24)

3.1 Synthesis and application in palladium-catalysed asymmetric allylic substitution of enantiopure cyclic &beta-iminophosphine ligands

Maria Zablocka, Marek Koprowski, Jean-Pierre Majoral, Mathieu Achard and Gérard Buono

(4)

3.1.1 Synthesis of (2,6-dimethyl-phenyl)-(1-phenyl-2,3,3a,8a-tetrahydro-1H-1-phospha-cyclopenta[α]inden-8-ylidene)-amines 1Rp

(1)

3.1.2 Synthesis of (E)-Methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate

(2)

3.1.3 Synthesis of benzyl(1,3-diphenylprop-2-enyl)amine

(1)

3.1.4 Conclusion

(1)

References

(1)

3.2 (9H,9'H,10H,10'H,11H,11H',13H,13'H,14H,14'H,15H,15'H-perfluorotricosane-12,12'-diyl)bis [(4S)-4-phenyl-2-oxazoline as a ligand for asymmetric palladium-catalysed alkylation of allylic acetates in fluorous media

Jérôme Bayardon and Denis Sinou

(7)

3.2.1 Synthesis of 2-iodo-1-(1H,1'H,2H,2'H,3H,3'H-perfluorooctyl)-3-propanol

(1)

3.2.2 Synthesis of 3-(1H,1'H,2H,2'H,3H,3'H-perfluorooctyl)-1-propanol

(1)

3.2.3 Synthesis of 3-(1H,1'H,2H,2'H,3H,3'H-perfluorooctyl)-1-iodopropane

(1)

3.2.4 Synthesis of (9H,9'H,10H,10'H,11H,11'H,13H,13'H,14H,14'H,15H,15'H-perfluorotricosane- 12,12'-diyl)-bis-[(4S)-4-phenyl-2-oxazoline]

(1)

3.2.5 Synthesis of (E)-Methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate

(1)

3.2.6 Conclusion

(1)

References

(1)

3.3 Facile synthesis of new axially chiral diphosphine complexes for asymmetric catalysis

Matthias Lotz, Gernot Kramer, Katja Tappe and Paul Knochel

(4)

3.3.1 Synthesis of (SFc)-1-[(S)-p-tolylsulfinyl]-2-[(o-diphenylphosphino)phenyl]ferrocene

(2)

3.3.2 Synthesis of (SFc)-1-diphenylphosphino-2-[(o-diphenylphosphino)phenyl]ferrocene

(1)

3.3.3 Conclusion

(1)

References

(1)

3.4 Chiral ferrocenyl-imino phosphines as ligands for palladium-catalysed enantioselective allylic alkylations

Pierluigi Barbaro, Claudio Bianchini, Giuliano Giambastiani and Antonio Togni

(9)

3.4.1 Synthesis of the precursor (R)-1-[(S)-2-bromoferrocenyl] ethyldiphenylphosphine

(1)

3.4.2 Synthesis of key precursor (R)-1-[(S)-2-formylferrocenyl] ethyldiphenylphosphine

(1)

3.4.3 Synthesis of (R)-1-[(S)-2-ferrocenylidene-ethyl-iminelethyldiphenyiphosphine

(1)

3.4.4 Conclusion

(1)

References

(3)

4 Suzuki Coupling Reactions

(32)

4.1 Palladium-catalysed borylation and Suzuki coupling (BSC) to obtain β-benzo[b]thienyldehydroamino acid derivatives

Ana S. Abreu, Paula M.T. Ferreira and Maria-João R.P. Queiroz

(4)

4.1.1 Synthesis of the E and Z isomers of the methyl ester of N-tert-butoxycarbonyl-β-bromodehydroaminobutyric acid

(1)

4.1.2 Synthesis of the methyl ester of N-tert-butoxycarbonyl-(Z)-[β-(2,3,7-trimethylbenzo[b]thien-6-yl]dehydro-aminobutyric acid

(2)

4.1.3 Conclusion

(1)

References

(1)

4.2 Palladium-catalysed cross-coupling reactions of 4-tosylcoumarins and arylboronic acids: synthesis of 4-arylcoumarin compounds

Jie Wu, Lisha Wang, Reza Fathi and Zhen Yang

(3)

4.2.1 Synthesis of 4-tosylcoumarins

(1)

4.2.2 Synthesis of 4-arylcoumarin

(1)

4.2.3 Conclusion

(1)

References

(1)

4.3 Cyclopropyl arenes, alkynes and alkenes from the in situ generation of B-cyclopropyl-9-BBN and the Suzuki-Miyaura coupling of aryl, alkynyl and alkenyl bromides

Ramon E. Huertas and John A. Soderquist

(3)

4.3.1 Synthesis of 4-cyclopropylbenzaldehyde

(2)

4.3.2 Conclusion

(1)

References

(1)

4.4 One-pot synthesis of unsymmetrical 1,3-dienes through palladium-catalysed sequential borylation of a vinyl electrophile by a diboron and cross-coupling with a distinct vinyl electrophile

Tatsuo Ishiyama and Norio Miyaura

(4)

4.4.1 Synthesis of 2-(1-cyclopentenyl)-1-decene

(3)

4.4.2 Conclusion

(1)

References

(1)

4.5 Pd(OAc)2/2-Aryl oxazoline catalysed Suzuki coupling reactions of aryl bromides and boronic acids

Bin Tao and David W. Boykin

(3)

4.5.1 Synthesis of 4-methoxybiphenyl

(1)

4.5.2 Conclusion

(1)

References

(1)

4.6 Palladium-catalysed reactions of haloaryl phosphine oxides: modular routes to functionalised ligands

Colin Baillie, Lijin Xu and Jianliang Xiao

(4)

4.6.1 Synthesis of 2-diphenylphosphinyl-2'-methoxybiphenyl via Suzuki coupling

(1)

4.6.2 Synthesis of 2-diphenylphosphino-2'-methoxybiphenyl

(1)

4.6.3 Conclusion

(1)

References

(1)

4.7 Bulky electron rich phosphino-amines as ligands for the Suzuki coupling reaction of aryl chlorides

Matthew L. Clarke and J. Derek Wool/ins

(5)

4.7.1 Synthesis of N-di-isopropylphosphino-N-methyl piperazine

(1)

4.7.2 Suzuki coupling reactions using isolated ligand and Pd2dba3.CHCl3 as catalyst

(1)

4.7.3 In situ ligand preparation and application in Suzuki coupling of 3-fluorobenzene with phenylboronic acid

(1)

4.7.4 Conclusion

(1)

References

(1)

4.8 Arylation of ketones, aryl amination and Suzuki-Miyaura cross coupling using a well-defined palladium catalyst bearing an N-heterocyclic carbene ligand

Nicholas Marion, Oscar Navarro, Roy A. Kelly III and Steven P. Nolan

(6)

4.8.1 Synthesis of 1,2-diphenyl-ethanone by ketone arylation

(2)

4.8.2 Synthesis of dibutyl-p-tolyl-amine by aryl amination

(1)

4.8.3 Synthesis of 4-methoxybiphenyl

(1)

4.8.4 Conclusion

(1)

References

(1)

5 Heck Coupling Reactions

(22)

5.1 Palladium-catalysed multiple and asymmetric arylations of vinyl ethers carrying co-ordinating nitrogen auxiliaries: synthesis of arylated ketones and aldehydes

Peter Nilsson and Mats Larhed

(8)

5.1.1 Triarylation: synthesis of N,N-dimethyl-2-[1,2,2-(triaryl) ethenyloxylethanamines with subsequent hydrolysisfurnishing 1,2,2-triaryl ethanones, Table 5.1

(3)

5.1.2 Terminal diarylation: synthesis of N,N-dimethyl-2-[2,2-diarylethenyloxy]ethanamine with subsequent hydrolysis furnishing diary] ethanals Table 5.2

(2)

5.1.3 Asymmetric Heck arylation: synthesis of 2-aryl-2-methylcyclopentanone

(2)

Conclusion

(1)

References

(1)

5.2 Palladium-catalysed highly regioselective arylation of electron-rich olefins

Lijin Xu, Jun Mo and Jianliang Xiao

100

(4)

5.2.1 Synthesis of 1-acetonaphthone

100

(2)

5.2.2 Synthesis of 3-acetylbenzonitrile

102

(2)

Conclusion

104

(1)

References

104

(1)

5.3 1-[4-(S)-tert-Butyl-2-oxazolin-2-yl]-2-(S)-(diphenylphosphino) ferrocene as a ligand for the palladium-catalysed intermolecular asymmetric Heck reaction of 2,3-dihydrofuran

Tim G. Kilroy, Yvonne M. Malone and Patrick J. Guiry

104

(9)

5.3.1 Synthesis of N-[1-(S)-(Hydroxymethyl)-2,2-dimethylpropyl]ferrocenecarboxamide

106

(1)

5.3.2 Synthesis of [4-(S)-tert-butyl-2-oxazolin-2-yl] ferrocene

107

(1)

5.3.3 Synthesis of 1-[4-(S)-tert-butyl-2-oxazolin-2-yl]-2-(S)-(diphenylphosphino)ferrocene

108

(2)

5.3.4 Asymmetric phenylation of 2,3-dihydrofuran

110

(2)

Conclusion

112

(1)

References

112

(1)

6 Sonogashira Coupling Reactions

113

(14)

6.1 Nonpolar biphasic catalysis: Suzuki- and Sonogashira coupling reactions

Anupama Datta and Herbert Plenio

113

(3)

6.1.1 Nonpolar biphasic Sonogashira reaction of 4-bromoaceto-phenone and phenylacetylene to 1-(4-phenylethynyl-phenyl)-ethanone

114

(1)

6.1.2 Nonpolar biphasic Suzuki reaction for the synthesis of1-biphenyl-4-yl-ethanone

115

(1)

Conclusion

116

(1)

References

116

(1)

6.2 Polystyrene-supported soluble palladacycle catalyst as recyclable catalyst for Heck, Suzuki and Sonogashira reactions

Chih-An Lin and Fen-Tair Luo

116

(12)

6.2.1 Synthesis of 3-bromo-4-methylacetophenone

117

(1)

6.2.2 Synthesis of 1-(3-bromo-4-methyl-phenyl)-ethanol

118

(2)

6.2.3 Synthesis of 3-bromo-4-methyl-styrene

120

(1)

6.2.4 Synthesis of 3-(diphenylphosphino)-4-methyl-styrene

121

(1)

6.2.5 Synthesis of trans-di(μ-acetato)-bis[3-(diphenylphos-phino)-4-styryl]dipalladium(II)

122

(1)

6.2.6 Synthesis of polymer-supported palladacycle catalyst

123

(1)

6.2.7 Synthesis of 1-[4-(2-phenylethynyl)phenyl]ethan-1-one via Sonogashira reaction by the use of polymer-supported palladacycle catalyst

124

(1)

Conclusion

125

(1)

Reference

125

(2)

7 Cross-Coupling Reactions

127

(28)

7.1 Cross-coupling reaction of alkyl halides with Grignard reagents in the presence of 1,3-butadiene catalysed by nickel, palladium, or copper

Jun Terao and Nobuaki Kambe

128

(5)

7.1.1 Synthesis of nonylcyclopropanc

128

(2)

7.1.2 Synthesis of 4-bromo-hexylbenzene

130

(1)

7.1.3 Synthesis of 1,1-diphenyl-1 nonene

131

(1)

Conclusion

132

(1)

References

132

(1)

7.2 Triorganoindium compounds as efficient reagents for palladium-catalysed cross-coupling reactions with aryl and vinyl electrophiles

Luis A. Sarandeses and José Pérez Sestelo

133

(5)

7.2.1 Preparation of triphenylindium

134

(1)

7.2.2 Synthesis of 4-acetylbiphenyl

134

(2)

7.2.3 Synthesis of 1,3-diphenyl-2-propen-1-one

136

(1)

Conclusion

137

(1)

References

138

(1)

7.3 Cross-coupling reactions catalysed by heterogeneous nickel-on-charcoal

Bryan A. Frieman and Bruce H. Lipshutz

138

(9)

7.3.1 Preparation of the heterogeneous catalyst: nickel-on-charcoal

139

(1)

7.3.2 Ni/C-catalysed Suzuki couplings: 2-cyanobiphenyl

140

(1)

7.3.3 Ni/C-catalysed aromatic aminations: N-(4-cyanophenyl)-morpholine

141

(1)

7.3.4 Ni/C-catalysed cross-couplings en route to allylated aromatics: toluene-4-sulfonic acid 2-(3,7,11,15,19,23,27,31, 35,39-decamethyltetraconta-2,6, 10,14,18,22,26,-30, 34,38-decaenyl)-5,6-dimethoxy-3-methylphenyl ester (coenzyme Q10 precursor)

142

(2)

7.3.5 Ni/C-catalysed reductions of aryl chlorides

144

(1)

7.3.6 Microwave assisted Ni/C-catalysed cross coupling of vinyl zirconocenes and aryl halides: 1-octenyl-4-trifluoromethylbenzene

145

(2)

Conclusion

147

(1)

References

147

(1)

7.4 Carbon-carbon bond formation using arylboron reagents with rhodium(I) catalysts in aqueous media

John Mancuso, Masahiro Yoshida and Mark Lautens

147

(9)

7.4.1 Synthesis of (E)-2-[2-(2-methylphenyl)-1- hexenyl]pyridine

148

(1)

7.4.2 Synthesis of methyl (2EZ)-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylate

149

(2)

7.4.3 Synthesis of methyl (1 S*,4R*,4aS*,9S*,9aS*)-2,3,4,4a,9,9ahexahydro-1H-1,4-methano-fluoren-9-ylacetate

151

(2)

References

153

(2)

8 Regioselective or Asymmetric 1,2-Addition to Aldehydes

155

(14)

8.1 Development of a highly regioselective metal-mediated allylation reaction in aqueous media

Kui-Thong Tan, Shu-Sin Chng, Hin-Soon Cheng and Teck-Peng Loh

156

(5)

8.1.1 Synthesis of 1-cyclohexylpent-3-en-ol using indium-mediated allylation

156

(1)

8.1.2 Synthesis of 1-cyclohexylpent-3-en-ol using tin-mediated allylation

157

(2)

8.1.3 Synthesis of 1-cyclohexylpent-3-en-ol usingzinc-mediated allylation

159

(1)

Conclusion

160

(1)

References

161

(1)

8.2 Boronic acids as aryl source for the catalysed enantioselective aryl transfer to aldehydes

Jens Rudolph and Carsten Bolm

161

(3)

8.2.1 Preparation of (S)-4-tolyl-phenyl methanol

161

(2)

Conclusion

163

(1)

References

163

(1)

8.3 Jacobsen's Salen as a chiral ligand for the chromium-catalysed addition of 3-chloro-propenyl pivalate to aldehydes: a catalytic asymmetric entry to syn-alk-l-ene-3,4-diols

Marco Lombardo, Sebastiano Licciulli, Stefano Morganti and Claudio Trombini

164

(5)

8.3.1 Synthesis of 3-chloro-propenyl pivalate

165

(1)

8.3.2 Synthesis of alk-1-ene-3,4-diols: Salen-Cr(II) catalysed addition of 3-chloro-propenyl pivalate to cyclohexanecarboxaldehyde

166

(2)

Conclusion

168

(1)

References

168

(1)

9 Olefin Metathesis Reactions

169

(12)

9.1 Highly active ruthenium (pre)catalysts for metathesis reactions

Syuzanna Harutyunyan, Anna Michrowska and Karol Grela

169

(5)

9.1.1 Synthesis of the ruthenium (pre)catalyst

170

(1)

9.1.2 Synthesis of 1-[(4-methylphenyl)sulfonyl]-2,3,6,7-tetrahydro-1H-azepine

171

(1)

Conclusion

172

(1)

References

173

(1)

9.2 A highly active and readily recyclable olefin metathesis catalyst

Stephen J. Connon, Aideen M. Dunne and Siegfried Blechert

174

(4)

9.2.1 Synthesis of polymer supported catalyst (3)

174

(2)

9.2.2 Ring-closing metathesis of an acyclic diene and subsequent catalyst recovery/reuse

176

(1)

Conclusion

177

(1)

References

177

(1)

9.3 Stereoselective synthesis of L-733,060

G. Bhaskar and B. Venkateswara Rao

178

(4)

9.3.1 Synthesis of (2S,3S)-N-tert-butoxycarbonyl-2-phenyl 1,2,3,6-tetrahydro-3-pyridinol

179

(1)

Conclusion

180

(1)

References

180

(1)

10 Cyclisation Reactions

181

(20)

10.1 Molecular sieves as promoters for the catalytic Pauson-Khand reaction

Jaime Blanco-Urgoiti, Gema Dominguez and Javier Pérez-Castells

182

(3)

10.1.1 Synthesis of 3aS*,5R*-5-hydroxy-3,3a,4,5-tetrahydrocyclopenta[a]naphthalen-2-one

182

(3)

Conclusion

185

(1)

References

185

(1)

10.2 Palladium(II)-catalysed cyclization of alkynes with aldehydes, ketones or nitriles initiated by acetoxypalladation of alkynes

Ligang Zhao and Xiyan Lu

185

(5)

10.2.1 Synthesis of 3-phenyl-3-hydroxy-4-(1'-acetoxyhexylidene)tetrahydrofuran

186

(1)

10.2.2 Synthesis of dimethyl 3-acetylamino-4-butyrylcyclo-pent-3-ene-1,1-dicarboxylate

187

(1)

Conclusion

188

(2)

References

190

(1)

10.3 Rhodium(I)-catalysed intramolecular alder-ene reaction and syntheses of functionalised a-methylene-y-butyrolactones and cyclopentanones

Minsheng He, Aiwen Lei and Xumu Zhang

190

(3)

10.3.1 Synthesis of (4-benzylidene-5-oxo-tetrahydro-furan-3-yl)-acetaldehyde

190

(1)

10.3.2 Synthesis of (3-oxo-2-pentylidene-cyclopentyl)-acetaldehyde

191

(1)

References

192

(1)

10.4 Rhodium-catalysed [2+2+2] cyclotrimerisation in an aqueous-organic biphasic system

Hiroshi Shinokubo and Koichiro Oshima

193

(3)

10.4.1 In situ preparation of a water-soluble rhodium catalyst from [RhCl(COD)]2 and trisodium salt of tris(m-sulfonatophenyl)phosphine (tppts)

193

(1)

10.4.2 Synthesis of 1,3,6,8,9,10,11,12,13-nonahydro-2,7-dioxacyclodeca[e]indene

194

(1)

Conclusion

195

(1)

References

196

(1)

10.5 Titanocene-catalysed transannular cyclisation of epoxygermacrolides: enantiospecific synthesis of eudesmanolides

Antonio Rosales, Juan M. Cuerva and J. Enrique Oltra

196

(6)

10.5.1 Preparation and titanocene-catalysed cyclization of epoxygermacrolide: synthesis of (+)-11β13-dihydroreynosin

197

(1)

10.5.2 Titanocene-catalysed cyclization of epoxygermacrolide in aqueous medium

198

(1)

References

199

(2)

11 Asymmetric Aldol and Michael Reactions

201

(24)

11.1 Direct catalytic asymmetric aldol reaction of a α-hydroxyketone promoted by an Et2Zn/linked-BINOL complex

Masakatsu Shibasaki, Shigeki Matsunaga and Naova Kumagai

202

(6)

11.1.1 Synthesis of (2R,3S)-2,3-dihydroxy-1-(2-methoxyphenyl)-5-phenyl-1-pentanone by the first generation Et2,Zn/Linked-BINOL = 2/1 complex

203

(2)

11.1.2 Synthesis of (2R,3S)-3-cyclohexyl-2,3-dihydroxy-1-(2-methoxyphenyl)-1-propanone by the second generation Et7Zn/linked-BINOL = 4/1 complex with MS3A

205

(2)

Conclusion

207

(1)

References

208

(1)

11.2 Highly enantioselective direct aldol reaction catalysed by a novel small organic molecule

Zhuo Tang, Liu-Zhu Gong, Ai-Qiao Mi and Yao-Zhong Jiang

208

(2)

11.2.1 Synthesis of (S,S,S)-pyrolidine-2-carboxylic acid (2'-hydroxyl-1',2'-diphenyl-ethyl)-amine (1)

208

(1)

11.2.2 Direct aldol reaction

209

(1)

Reference

210

(1)

11.3 Direct catalytic asymmetric Michael reaction of α-hydroxyketone promoted by Et2Zn/linked-BINOL complex

Masakatsu Shibasaki, Shigeki Matsunaga and Naova Kumagai

210

(6)

11.3.1 Synthesis of (2R)-2-hydroxy-1-(2-methoxyphenyl)-1,5-hexanedione by the first generation Et,Zn/linked-BINOL = 2/1 complex

211

(2)

11.3.2 Synthesis of (2R)-2-hydroxy-1-(2-methoxyphenyl)-1,5-hexanedione by the second Et2Zn/linked-BINOL 4/1 complex with MS 3A

213

(32)

Conclusion

245

References

215

(1)

11.4 Catalytic enantioselective Michael reaction catalysed by well-defined chiral ruthenium-amido complexes

Masahito Watanabe, Kunihiko Murata, and Takao Ikariya

216

(10)

11.4.1 Synthesis of Ru[(R,R)-Tsdpenl(η6-arenc): Ru[(R,R;-Tsdpen](ρ-cymene), ((R,R)-TsDPEN = 1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) (p-cymene = η6-1-CH3-4-CH(CH3)2C6H4)8b, Ru[(R,R)-Tsdpen](hmb), and Ru[(R,R)-Msdpen](hmb)

217

(2)

11.4.2 Synthesis of (S)-3-di(methoxycarbonyl)methyl-lcyclopentanone from the Michael reaction of dimethyl malonate and 2-cyclopenten-1-one catalysed by Ru[(R,R)-Tsdpen](hmb)

219

(1)

11.4.3 Synthesis of (S)-3-di(methoxycarbonyl)methyl-lcyclopentanone from the Michael reaction of dimethyl malonate and cyclopentenone catalyzed by Ru[(R,R)-N-Msdpen](hmb)

220

(1)

11.4.4 Synthesis (S)-3-di(methoxycarbonyl)methyl-1-cyclohexanone from the Michael reaction of dimethyl malonate and cyclohexenone catalysed by Ru[(R,R)- Msdpen](hmb)

221

(1)

Conclusion

222

(1)

References

223

(2)

12 Stereoselective Hydroformylation, Carbonylation and Carboxylation Reactions

225

(26)

12.1 Ortho-diphenylphosphanylbenzoyl-(o-DPPB) directed diastereoselective hydroformylation of allylic alcohols

Bernhard Breit

226

(4)

12.1.1 Synthesis of 1RS-(±)-[(1-iso-propyl-2-methyl)prop-2-enyll (2-diphenylphosphanyl)benzoate

227

(1)

12.1.2 Synthesis of (1R*,2R*)-(±)-[(1-Isopropyl-4-oxo-2-methyl)butyl] (2-diphenylphosphanyl)-benzoate

228

(1)

Conclusion

229

(1)

References

230

(1)

12.2 The synthesis and application of ESPHOS: A new diphosphorus ligand for the hydroformylation of vinyl acetate

Martin Wills and Simon W. Breeden

230

(8)

12.2.1 Synthesis of ortho-diazobromobenzene

232

(1)

12.2.2 Synthesis of ortho-(dichlorophosphine) bromobenzene

232

(1)

12.2.3 Synthesis of ortho-bis(dimethylamino) bromobenzene

233

(1)

12.2.4 Synthesis of 1,2-bis(dimethylaminophosphanyl)benzene

234

(1)

12.2.5 Synthesis of ESPHOS (1)[²]

235

(1)

12.2.6 Hydroformylation of vinyl acetate[³]

236

(1)

Conclusion

237

(1)

References

237

(1)

12.3 Platinum-catalysed asymmetric hydroformylation of styrene

Submitted by Stefánia Cserépi-Szücs and József Bakos

238

(6)

12.3.1 Rhodium-catalysed asymmetric hydroformylation of styrene

239

(1)

12.3.2 Synthesis of (4R,6R)-4,6-di methyl-2-chloro-1,3,2-dioxaphosphorinane

240

(1)

12.3.3 Synthesis of (2R,4R)-2,4-bis[(4R,6R)-4,6-dimethyl-1,3,2-dioxaphos-phorinane-2-yloxy]-pentane

241

(2)

12.3.4 Determinataion of optical purity: synthesis of mixture of 2-phenylpropionic acid and 3-phenylpropionic acid

243

(1)

12.4 Phosphine-free dimeric palladium (II) complex for the carbonylation of aryl iodides

C. Ramesh, Y. Kubota and Y. Sugi

244

(3)

12.4.1 Synthesis of the dimeric oximepalladacycle

244

(1)

12.4.2 Synthesis of phenyl biphenyl-4-carboxylatc

245

(2)

Conclusion

247

(1)

Reference

247

(1)

12.5 Carboxylation of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical carbon dioxide

Tomoko Matsuda, Tadao Harada, Toru Nagasawa and Kaoru Nakamura

247

(4)

12.5.1 Construction of supercritical carbon dioxide reaction system

248

(1)

12.5.2 Carboxylation of pyrrole to pyrrole-2-carboxylate

249

(1)

Conclusion

250

(1)

References

250

(1)

Index

251

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Metal Catalysed Carbon-Carbon Bond-Forming Reactions, Volume 3

Summary

Author Biography

Table of Contents

Supplemental Materials