Classics in Stereoselective Synthesis

, by Carreira, Erick M.; Kvaerno, Lisbet

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ISBN: 9783527324521 | 3527324526
Cover: Hardcover
Copyright: 2/9/2009

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This book provides a noteworthy compilation of the groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modern practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid and continuing developments in the field. The work also features illustrative examples of drug and natural product syntheses, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the construction of stereochemically complex structures. From the contents: "Macrocyclic stereocontrol "Carbonyl addition reactions "alpha-Functionalization of enolates "Aldol and allylation reactions "Chiral acetals "Alkene hydroboration, reduction, and oxidation "Additions to C=N bonds and synthesis of amino acids "Conjugate additions "Chiral carbanions "Metal-catalyzed allylations "Cyclopropanations and CH-insertion reactions "Sigmatropic rearrangements "Diels-Alder and hetero-Diels-Alder reactions "[3+2]- and [2+2]-cycloaddition reactions

Preface	p. XIII
Acknowledgement	p. XIX
Macrocyclic Stereocontrol	p. 1
Introduction	p. 1
Background	p. 1
Conformational Control in Medium-Sized Rings	p. 4
Asymmetric Synthesis with Medium-Sized Rings	p. 6
Case Studies in Natural Products Total Synthesis	p. 8
Macrocyclic Stereocontrol in Cyclic Peptides	p. 14
Appendix: Macrocycle Formation	p. 14
Conclusion	p. 15
References	p. 16
Carbonyl Addition Reactions	p. 19
Introduction	p. 19
Non-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects	p. 21
1,2-Asymmetric Induction Predicated on Chelation Control	p. 25
1,3-Asymmetric Induction from Cb Stereogenic Centers	p. 29
Asymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction)	p. 37
Catalytic Enantioselective Carbonyl Additions of Organozinc Species	p. 38
Enantioselective Ketone Reduction	p. 42
Enzymatic Reduction of Ketones	p. 49
Enantioselective Formation of Cyanohydrins	p. 50
Enantioselective Alkyne Additions	p. 54
Asymmetric Carbonyl-Ene Reactions	p. 57
Conclusion	p. 59
References	p. 59
a-Functionalizations of Enolates	p. 69
Introduction	p. 69
Diastereoselective a-Alkylations of Chiral Enolates	p. 71
Heteroatom-Substituted Enolates	p. 75
Asymmetric Enolate Alkylations Using Chiral Auxiliaries	p. 78
Enantioselective Enolates Alkylations	p. 89
a-Hydroxylations of Enolates	p. 91
a-Halogenations of Enolates	p. 94
Conclusion	p. 96
References	p. 97
Aldol Reactions	p. 103
Introduction	p. 103
Chiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller Groups	p. 107
Imides	p. 107
Esters	p. 112
Tethered Amides	p. 114
Chiral Boron Reagents	p. 115
Substrate Control with Chiral Carbonyl Compounds	p. 118
Catalytic Enantioselective Aldol Reactions	p. 123
Proline-Catalyzed Aldol Additions	p. 123
In Situ Direct Generation of Enolates and Their Asymmetric Aldol Addition Reactions	p. 124
Enolsilanes and Stannanes	p. 127
Conclusion	p. 143
References	p. 143
Allylations of C=O Bonds	p. 153
Introduction	p. 153
Reactivity of Allylmetal Reagents	p. 156
Boronate Additions	p. 156
Enantioselective Additions of Optically Active Allylic Boron Reagents	p. 158
Diastereoselective Allylations with Chiral Boron Reagents	p. 164
Mechanistic Aspects-Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to Aldehydes	p. 167
Chelation Control in the Allylation of a-and b-Alkoxy Aldehydes	p. 168
Allylchromium Reagents	p. 171
Diastereoselective Allylations with Chiral Silanes and Stannanes	p. 172
Catalytic Asymmetric Allylations	p. 176
Conclusion	p. 180
References	p. 180
Chiral Acetals	p. 187
Introduction	p. 187
Diastereoselective Reactions of Chiral Acetals	p. 188
Glycosylations	p. 198
Spiroketals in Natural Product Synthesis	p. 204
Conclusion	p. 208
References	p. 209
Alkene Hydroboration	p. 215
Introduction	p. 215
Hydroborations with Acyclic Stereocontrol	p. 216
Metal-Catalyzed Hydroborations	p. 226
Asymmetric Hydroborations with Chiral Boranes	p. 227
Catalytic Asymmetric Hydroborations, Hydrosilylation, and Hydroalumination	p. 229
Conclusion	p. 232
References	p. 232
Reductions of Olefins	p. 235
Introduction	p. 235
Diastereoselective Olefin Reductions by Catalytic Hydrogenation	p. 236
Alternative Methods for Diastereoselective Olefin Reductions	p. 243
Catalytic Asymmetric Olefin Hydrogenations	p. 247
Conclusion	p. 256
References	p. 256
Oxidations of Olefins	p. 263
Introduction	p. 263
Diastereoselective Epoxidations	p. 264
Enantioselective Epoxidations	p. 268
Asymmetric Ring-Opening of Epoxides	p. 277
Synthesis of Aziridines	p. 282
Iodolactonizations and Other Olefin Cyclizations Induced by Electrophiles	p. 285
Diastereoselective Dihydroxylations of Olefins	p. 291
Enantioselective Dihydroxylations of Olefins	p. 296
Enantioselective Aminohydroxylation of Olefins	p. 300
Conclusion	p. 302
References	p. 303
Amino Acids	p. 315
Introduction	p. 315
Enantioselective Hydrogenations of a, b-Didehydroamino Acids	p. 315
Enolate Alkylations in the Presence of Chiral Auxiliaries	p. 321
Alkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer Catalysts	p. 324
Enolate Aminations	p. 327
Enzymatic Syntheses of a-Amino Acids	p. 329
Catalytic Asymmetric Strecker Reactions	p. 330
Conclusion	p. 334
References	p. 336
Additions to C=N Bonds	p. 343
Introduction	p. 343
Substrate-Controlled Diastereoselective Additions to C=N Bonds	p. 344
Additions to Imine Derivatives Bearing N-Bound Auxiliaries	p. 349
Formation of ß-Lactams Through Staudinger Reactions	p. 354
Intramolecular Diastereoselective Iminium Ion Cyclizations	p. 356
Diastereoselective Mannich Cyclizations in Complex Molecule Synthesis	p. 356
Acyliminium Ion and Related Cyclizations	p. 358
Pictet-Spengler Reactions	p. 359
Catalytic Asymmetric Reductions of Imines and Imine Derivatives	p. 362
Catalytic Enantioselective Mannich and Mannich-Type Reactions	p. 366
Enantioselective Additions of Carbon Nucleophiles to C=N Bonds	p. 370
Enantioselective Allylations of C=N Bonds	p. 370
Catalytic Enantioselective Imino-Ene Reactions	p. 372
Catalytic Enantioselective Additions of Alkylzinc Reagents to Imines	p. 373
Catalytic Enantioselective Arylations of Imines	p. 375
Catalytic Enantioselective Aza-Henry Reactions	p. 376
Catalytic Enantioselective Cyanations of Ketimines	p. 377
Conclusion	p. 378
References	p. 379
Conjugate Additions	p. 389
Introduction	p. 389
Diastereoselective Conjugate Additions	p. 390
Diastereoselective Conjugate Additions with Use of Chiral Auxiliaries	p. 395
Enantioselective Conjugate Additions of Enolates and other Stabilized Carbon Nucleophiles	p. 401
Enantioselective Conjugate Additions of Organometallic Species	p. 407
Enantioselective Conjugate Additions of Radicals	p. 414
Enantioselective Conjugate Additions of Heteroatom Nucleophiles	p. 415
Conjugate Reductions	p. 417
Catalytic Enantioselective Stetter Reactions	p. 420
Conclusion	p. 421
References	p. 421
Chiral Carbanions	p. 431
Introduction	p. 431
Organolithium Reagents by Transmetalation of Organostannanes	p. 432
Carbanions by Reductive Methods	p. 434
Chiral Carbanions by Deprotonation	p. 436
Sulfoxide-and Phosphorus-Stabilized Carbanions	p. 443
Metal-Mediated Enantioselective Olefin Functionalizations	p. 446
Conclusion	p. 451
References	p. 452
Metal-Catalyzed Allylations	p. 457
Introduction	p. 457
Diastereoselective Palladium-Catalyzed Allylation Reactions	p. 457
Enantioselective Palladium-Catalyzed Allylation Reactions	p. 461
Iridium-Catalyzed Enantioselective Allylation Reactions	p. 466
Copper-Catalyzed SN2' Allylation Reactions	p. 468
Enantioselective Allylation Reactions Catalyzed by Other Transition Metals	p. 471
Asymmetric Ring-Opening Reactions of Unsaturated Heterocycles	p. 474
Conclusion	p. 476
References	p. 477
Cyclopropanations and C-H Insertion Reactions	p. 483
Introduction	p. 483
Diastereoselective Cyclopropanations with Carbenoids Generated from Diazoalkanes	p. 485
Enantioselective Cyclopropanations with Carbenoids Generated from Diazoalkanes	p. 488
Diastereoselective Simmons-Smith Cyclopropanations	p. 493
Enantioselective Simmons-Smith Cyclopropanations	p. 496
Alternative Classes of Cyclopropanations	p. 497
Diastereoselective C-H Insertions	p. 501
Catalytic Enantioselective C-H Insertions	p. 503
Aminations of C-H Bonds	p. 506
Conclusion	p. 508
References	p. 509
Sigmatropic Rearrangements	p. 515
Introduction	p. 515
Claisen and Claisen-Type [3,3]-Sigmatropic Rearrangements	p. 516
Simple Diastereoselectivity in Clasien Rearrangements	p. 518
Diastereoselective Claisen Rearrangements in Complex Molecule Synthesis	p. 520
Diastereoselective Claisen Rearrangements Using Chiral Auxiliaries	p. 525
Enantioselective Claisen Rearrangements	p. 526
Cope and Cope-Type [3,3]-Sigmatropic Rearrangements	p. 528
[2,3]-Sigmatropic Rearrangements	p. 532
Witting Rearrangements	p. 534
Sulfoxide, Ammonium, and Oxonium Ylide Rearrangements	p. 536
Ene Reactions	p. 539
Nazarov Cyclizations	p. 543
Conclusion	p. 544
References	p. 545
Diels-Alder and Hetero-Diels-Alder Reactions	p. 551
Introduction	p. 551
Diastereoselective Intermolecular Diels-Alder Reactions	p. 554
Diastereoselective Intermolecular Diels-Alder Reactions	p. 556
Diastereoselective Diels-Alder Reactions Using Chiral Auxiliaries	p. 560
Catalytic Enantioselective Diels-Alder Reactions	p. 564
Diastereoselective Hetero-Diels-Alder Reactions	p. 572
Enantioselective Hetero-Diels-Alder Reactions	p. 576
Conclusion	p. 580
References	p. 581
[3+2]-and [2+2]-Cycloaddition Reactions	p. 589
Introduction	p. 589
Substrate-Controlled Diastereoselective [1,3]-Dipolar Cycloadditions	p. 590
Diastereoselective [1,3]-Dipolar Cycloadditions Using Chiral Auxiliaries	p. 596
Catalytic Enantioselective [1,3]-Dipolar Cycloadditions	p. 599
[3+2]-Cycloadditions with Trimethylenemethane Equivalents	p. 604
Ketene Cycloadditions	p. 607
Photochemical [2+2]-Cycloadditions	p. 610
Conclusion	p. 615
References	p. 616
Index	p. 623
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Classics in Stereoselective Synthesis

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