Asymmetric Fluoroorganic Chemistry Synthesis,

The substitution of fluorine in an organic molecule increases its chemical stability and changes its reactivity, sometimes leading to substantially more effective medicines, pesticides, and herbicides. This book collects current work on the synthesis of these compounds.

Preface

ix

Fluorine-Containing Chiral Compounds of Biomedical Interest

1

(21)

Robert Filler

REAGENT-CONTROLLED ASYMMETRIC SYNTHESIS

Asymmetric Synthesis of Fluoroorganic Compounds via Chiral Organoboranes

22

(16)

P. V. Ramachandran

Herbert C. Brown

Catalytic Asymmetric Synthesis of Fluoroorganic Compounds: Mukaiyama--Aldol and Henry Reactions

38

(14)

Katsuhiko Iseki

Asymmetric Fluorination of α-Amino Ketones: Synthesis of Monofluoroketomethylene Peptide Isosteres and Related Compounds

52

(8)

Robert V. Hoffman

Junhua Tao

Asymmetric Friedel-Crafts Reactions with Fluoral Catalyzed by Chiral Binaphthol-Derived Titanium Catalysts

60

(14)

Akihiro Ishii

Koichi Mikami

SUBSTRATE-CONTROLLED ASYMMETRIC SYNTHESIS

Biomimetic, Reducing Agent-Free Reductive Amination of Fluorocarbonyl Compounds: Practical Asymmetric Synthesis of Enantiopure Fluoroamines and Amino Acids

74

(10)

Vadim A. Soloshonok

Stereoselective and Enantioselective Synthesis of New Fluoroalkyl Peptidomimetic Units: Amino Alcohols and Isoserines

84

(14)

Ahmed Abouabdellah

Jean-Pierre Begue

Daniele Bonnet-Delpon

Andrei Kornilov

Isabelle Rodrigues

Truong Thi Thanh Nga

Asymmetric Synthesis of Fluoroalkyl Amino Compounds via Chiral Sulfoxides

98

(19)

Pierfrancesco Bravo

Luca Bruche

Marcello Crucianelli

Fiorenza Viani

Matteo Zanda

Studies Toward the Syntheses of Functionalized, Fluorinated Allyl Alcohols

117

(10)

P. V. Ramachandran

M. Venkat Ram Reddy

Michael T. Rudd

Stereoselective Synthesis of β-Fluoroalkyl β-Amino Alcohols Units

127

(15)

Matteo Zanda

Pierfrancesco Bravo

Alessandro Volonterio

Diastereoselective Construction of Novel Sugars Containing Variously Fluorinated Methyl Groups as Intermediates for Fluorinated Aldols

142

(16)

Takashi Yamazaki

Shuichi Hiraoka

Tomoya Kitazume

SYNTHESIS OF FLUOROORGANIC TARGETS

Synthesis of Enantiopure Fluorine-Containing Taxoids and Their Use as Anticancer Agents as well as Probes for Biomedical Problems

158

(24)

Iwao Ojima

Tadashi Inoue

John C. Slater

Songnian Lin

Scott D. Kuduk

Subrata Chakravarty

John J. Walsh

Thierry Cresteil

Bernard Monsarrat

Paula Pera

Ralph J. Bernacki

The Synthesis of a Series of Fluorinated Tribactams

182

(12)

Ferenc Gyenes

Andrei Kornilov

John T. Welch

BIOORGANIC SYNTHESIS OF ASYMMETRIC FLUOROORGANIC COMPOUNDS

Chemical and Biochemical Approaches to the Enantiomers of Chiral Fluorinated Catecholamines and Amino Acids

194

(16)

K. L. Kirk

B. Herbert

S.-F. Lu

B. Jayachandran

W. L. Padgett

O. Olufunke

J. W. Daly

G. Haufe

K. W. Laue

Natural Products Containing Fluorine and Recent Progress in Elucidating the Pathway of Fluorometabolite Biosynthesis in Streptomyces cattleya

210

(16)

D. O'Hagan

D. B. Harper

ASYMMETRIC FLUOROORGANIC CHEMISTRY IN MATERIALS CHEMISTRY

Synthetic Aspects of Fluorine-Containing Chiral Liquid Crystals

226

(13)

Tamejiro Hiyama

Tetsuo Kusumoto

Hiroshi Matsutani

Resolution of Racemic Perfluorocarbons through Self-Assembly Driven by Electron Donor-Acceptor Intermolecular Recognition

239

(16)

Maria Teresa Messina

Pierangelo Metrangolo

Giuseppe Resnati

Catalytic Asymmetric Synthesis of Diastereomeric α- or β-CF3 Liquid Crystalline Molecules: Conformational Probe for Anti-Ferroelectricity and Self-Assembly for Spontaneous Chiral Resolution of the Racemates

255

(17)

Koichi Mikami

ASYMMETRIC FLUOROORGANIC CHEMISTRY IN AGROCHEMISTRY AND PHARMACY

Chiral 3-Aryl-4-halo-5-(trifluoromethyl)pyrazoles: Synthesis and Herbicidal Activity of Enantiomeric Lactate Derivatives of Aryl-Pyrazole Herbicides

272

(10)

Bruce C. Hamper

Kindrick L. Leschinsky

Deborah A. Mischke

S. Douglas Prosch

Chiral Fluorinated Anesthetics

282

(13)

Keith Ramig

INDEXES

Author Index

294

(1)

Subject Index

295

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Asymmetric Fluoroorganic Chemistry Synthesis, Applications, and Future Directions

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Asymmetric Fluoroorganic Chemistry Synthesis, Applications, and Future Directions

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Table of Contents

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