| Preface |
|
xiii | |
| Abbreviations |
|
xv | |
|
|
|
1 | (70) |
|
The Significance of Chirality and Stereoisomeric Discrimination |
|
|
3 | (4) |
|
|
|
7 | (9) |
|
|
|
7 | (1) |
|
|
|
8 | (8) |
|
Determining Enantiomer Composition |
|
|
16 | (13) |
|
Measuring Specific Rotation |
|
|
17 | (2) |
|
The Nuclear Magnetic Resonance Method |
|
|
19 | (4) |
|
Some Other Reagents for Nuclear Magnetic Resonance Analysis |
|
|
23 | (1) |
|
Determining the Enantiomer Composition of Chiral Glycols or Cyclic Ketones |
|
|
24 | (1) |
|
Chromatographic Methods Using Chiral Columns |
|
|
25 | (3) |
|
Capillary Electrophoresis with Enantioselective Supporting Electrolytes |
|
|
28 | (1) |
|
Determining Absolute Configuration |
|
|
29 | (18) |
|
X-Ray Diffraction Methods |
|
|
30 | (2) |
|
|
|
32 | (3) |
|
The Chemical Interrelation Method |
|
|
35 | (1) |
|
|
|
36 | (3) |
|
|
|
39 | (1) |
|
Nuclear Magnetic Resonance Method for Relative Configuration Determination |
|
|
40 | (7) |
|
General Strategies for Asymmetric Synthesis |
|
|
47 | (9) |
|
|
|
48 | (1) |
|
Acyclic Diastereoselective Approaches |
|
|
49 | (4) |
|
Double Asymmetric Synthesis |
|
|
53 | (3) |
|
Examples of Some Complicated Compounds |
|
|
56 | (6) |
|
Some Common Definitions in Asymmetric Synthesis and Stereochemistry |
|
|
62 | (3) |
|
|
|
65 | (6) |
|
α-Alkylation and Catalytic Alkylation of Carbonyl Compounds |
|
|
71 | (64) |
|
|
|
71 | (2) |
|
|
|
73 | (25) |
|
Intra-annular Chirality Transfer |
|
|
74 | (4) |
|
Extra-annular Chirality Transfer |
|
|
78 | (1) |
|
Chelation-Enforced Intra-annular Chirality Transfer |
|
|
79 | (19) |
|
Preparation of Quaternary Carbon Centers |
|
|
98 | (5) |
|
Preparation of α-Amino Acids |
|
|
103 | (1) |
|
Nucleophilic Substitution of Chiral Acetal |
|
|
103 | (4) |
|
Chiral Catalyst-Induced Aldehyde Alkylation: Asymmetric Nucleophilic Addition |
|
|
107 | (11) |
|
Catalytic Asymmetric Additions of Dialkylzinc to Ketones: Enantioselective Formation of Tertiary Alcohols |
|
|
118 | (1) |
|
Asymmetric Cyanohydrination |
|
|
118 | (6) |
|
Asymmetric α-Hydroxyphosphonylation |
|
|
124 | (3) |
|
|
|
127 | (1) |
|
|
|
127 | (8) |
|
Aldol and Related Reactions |
|
|
135 | (60) |
|
|
|
135 | (3) |
|
Substrate-Controlled Aldol Reaction |
|
|
138 | (12) |
|
Oxazolidones as Chiral Auxiliaries: Chiral Auxiliary-Mediated Aldol-Type Reactions |
|
|
138 | (4) |
|
Pyrrolidines as Chiral Auxiliaries |
|
|
142 | (3) |
|
Aminoalcohols as the Chiral Auxiliaries |
|
|
145 | (3) |
|
Acylsultam Systems as the Chiral Auxiliaries |
|
|
148 | (2) |
|
|
|
150 | (1) |
|
Reagent-Controlled Aldol Reactions |
|
|
150 | (5) |
|
Aldol Condensations Induced by Chiral Boron Compounds |
|
|
150 | (1) |
|
Aldol Reactions Controlled by Corey's Reagents |
|
|
151 | (3) |
|
Aldol Condensations Controlled by Miscellaneous Reagents |
|
|
154 | (1) |
|
Chiral Catalyst-Controlled Asymmetric Aldol Reaction |
|
|
155 | (10) |
|
|
|
155 | (4) |
|
Asymmetric Aldol Reactions with a Chiral Ferrocenylphosphine-Gold(I) Complex |
|
|
159 | (1) |
|
Asymmetric Aldol Reactions Catalyzed by Chiral Lewis Acids |
|
|
160 | (3) |
|
Catalytic Asymmetric Aldol Reaction Promoted by Bimetallic Catalysts: Shibasaki's System |
|
|
163 | (2) |
|
Double Asymmetric Aldol Reactions |
|
|
165 | (2) |
|
Asymmetric Allylation Reactions |
|
|
167 | (12) |
|
|
|
168 | (6) |
|
|
|
174 | (1) |
|
Other Catalytic Asymmetric Allylation Reactions |
|
|
175 | (4) |
|
Asymmetric Allylation and Alkylation of Imines |
|
|
179 | (7) |
|
Other Types of Addition Reactions: Henry Reaction |
|
|
186 | (2) |
|
|
|
188 | (1) |
|
|
|
188 | (7) |
|
|
|
195 | (72) |
|
Asymmetric Epoxidation of Allylic Alcohols: Sharpless Epoxidation |
|
|
195 | (9) |
|
The Characteristics of Sharpless Epoxidation |
|
|
197 | (2) |
|
|
|
199 | (1) |
|
Modifications and Improvements of Sharpless Epoxidation |
|
|
200 | (4) |
|
Selective Opening of 2,3-Epoxy Alcohols |
|
|
204 | (13) |
|
External Nucleophilic Opening of 2,3-Epoxy Alcohols |
|
|
205 | (2) |
|
Opening by Intramolecular Nucleophiles |
|
|
207 | (2) |
|
Opening by Metallic Hydride Reagents |
|
|
209 | (1) |
|
Opening by Organometallic Compounds |
|
|
210 | (1) |
|
Payne Rearrangement and Ring-Opening Processes |
|
|
211 | (3) |
|
Asymmetric Desymmetrization of meso-Epoxides |
|
|
214 | (3) |
|
Asymmetric Epoxidation of Symmetric Divinyl Carbinols |
|
|
217 | (4) |
|
Enantioselective Dihydroxylation of Olefins |
|
|
221 | (11) |
|
Asymmetric Aminohydroxylation |
|
|
232 | (5) |
|
Epoxidation of Unfunctionalized Olefins |
|
|
237 | (12) |
|
Catalytic Enantioselective Epoxidation of Simple Olefins by Salen Complexes |
|
|
237 | (6) |
|
Catalytic Enantioselective Epoxidation of Simple Olefins by Porphyrin Complexes |
|
|
243 | (1) |
|
Chiral Ketone-Catalyzed Asymmetric Oxidation of Unfunctionalized Olefins |
|
|
244 | (5) |
|
Catalytic Asymmetric Epoxidation of Aldehydes |
|
|
249 | (1) |
|
Asymmetric Oxidation of Enolates for the Preparation of Optically Active α-Hydroxyl Carbonyl Compounds |
|
|
250 | (5) |
|
Substrate-Controlled Reactions |
|
|
251 | (1) |
|
Reagent-Controlled Reactions |
|
|
252 | (3) |
|
Asymmetric Aziridination and Related Reactions |
|
|
255 | (5) |
|
|
|
255 | (2) |
|
Regioselective Ring Opening of Aziridines |
|
|
257 | (3) |
|
|
|
260 | (1) |
|
|
|
261 | (6) |
|
Asymmetric Diels-Alder and Other Cyclization Reactions |
|
|
267 | (64) |
|
|
|
268 | (9) |
|
|
|
269 | (1) |
|
|
|
270 | (3) |
|
Chiral α,β-Unsubstituted N-Acyloxazolidinones |
|
|
273 | (1) |
|
Chiral Alkoxy Iminium Salt |
|
|
273 | (4) |
|
Chiral Sulfinyl-Substituted Compounds as Dienophiles |
|
|
277 | (1) |
|
|
|
277 | (1) |
|
Double Asymmetric Cycloaddition |
|
|
278 | (1) |
|
Chiral Lewis Acid Catalysts |
|
|
279 | (11) |
|
|
|
280 | (2) |
|
Chiral Lanthanide Catalyst |
|
|
282 | (1) |
|
Bissulfonamides (Corey's Catalyst) |
|
|
282 | (1) |
|
Chiral Acyloxy Borane Catalysts |
|
|
283 | (2) |
|
Bronsted Acid--Assisted Chiral Lewis Acid Catalysts |
|
|
285 | (2) |
|
|
|
287 | (2) |
|
Amino Acid Salts as Lewis Acids for Asymmetric Diels-Alder Reactions |
|
|
289 | (1) |
|
Hetero Diels-Alder Reactions |
|
|
290 | (11) |
|
Oxo Diels-Alder Reactions |
|
|
290 | (6) |
|
Aza Diels-Alder Reactions |
|
|
296 | (5) |
|
Formation of Quaternary Stereocenters Through Diels-Alder Reactions |
|
|
301 | (1) |
|
Intramolecular Diels-Alder Reactions |
|
|
301 | (5) |
|
Retro Diels-Alder Reactions |
|
|
306 | (2) |
|
Asymmetric Dipolar Cycloaddition |
|
|
308 | (5) |
|
Asymmetric Cyclopropanation |
|
|
313 | (9) |
|
Transition Metal Complex--Catalyzed Cyclopropanations |
|
|
314 | (5) |
|
The Catalytic Asymmetric Simmons-Smith Reaction |
|
|
319 | (3) |
|
|
|
322 | (1) |
|
|
|
323 | (8) |
|
Asymmetric Catalytic Hydrogenation and Other Reduction Reactions |
|
|
331 | (66) |
|
|
|
331 | (24) |
|
Chiral Phosphine Ligands for Homogeneous Asymmetric Catalytic Hydrogenation |
|
|
332 | (2) |
|
Asymmetric Catalytic Hydrogenation of C=C Bonds |
|
|
334 | (21) |
|
Asymmetric Reduction of Carbonyl Compounds |
|
|
355 | (18) |
|
|
|
356 | (3) |
|
Transition Metal-Complex Catalyzed Hydrogenation of Carbonyl Compounds |
|
|
359 | (8) |
|
The Oxazaborolidine Catalyst System |
|
|
367 | (6) |
|
Asymmetric Reduction of Imines |
|
|
373 | (4) |
|
Asymmetric Transfer Hydrogenation |
|
|
377 | (7) |
|
Asymmetric Hydroformylation |
|
|
384 | (4) |
|
|
|
388 | (1) |
|
|
|
389 | (8) |
|
Applications of Asymmetric Reactions in the Synthesis of Natural Products |
|
|
397 | (54) |
|
The Synthesis of Erythronolide A |
|
|
397 | (3) |
|
The Synthesis of 6-Deoxyerythronolide |
|
|
400 | (3) |
|
The Synthesis of Rifamycin S |
|
|
403 | (9) |
|
Kishi's Synthesis in 1980 |
|
|
404 | (4) |
|
Kishi's Synthesis in 1981 |
|
|
408 | (1) |
|
|
|
409 | (3) |
|
The Synthesis of Prostaglandins |
|
|
412 | (6) |
|
|
|
414 | (1) |
|
Synthesis of the ω-Side Chain |
|
|
415 | (2) |
|
The Enantioselective Synthesis of (R)-4-Hydroxy-2-Cyclopentenone |
|
|
417 | (1) |
|
The Total Synthesis of Taxol--A Challenge and Opportunity for Chemists Working in the Area of Asymmetric Synthesis |
|
|
418 | (27) |
|
Synthesis of Baccatin III, the Polycyclic Part of Taxol |
|
|
419 | (23) |
|
Asymmetric Synthesis of the Taxol Side Chain |
|
|
442 | (3) |
|
|
|
445 | (1) |
|
|
|
446 | (5) |
|
Enzymatic Reactions and Miscellaneous Asymmetric Syntheses |
|
|
451 | (58) |
|
Enzymatic and Related Processes |
|
|
451 | (7) |
|
Lipase/Esterase-Catalyzed Reactions |
|
|
452 | (2) |
|
|
|
454 | (1) |
|
Enantioselective Microbial Oxidation |
|
|
455 | (1) |
|
|
|
456 | (2) |
|
Biocatalysts from Cultured Plant Cells |
|
|
458 | (1) |
|
|
|
458 | (26) |
|
Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine Complex |
|
|
458 | (1) |
|
Asymmetric Hydrosilyation of Olefins |
|
|
459 | (1) |
|
Synthesis of Chiral Biaryls |
|
|
460 | (4) |
|
The Asymmetric Kharasch Reaction |
|
|
464 | (1) |
|
Optically Active Lactones from Metal-Catalyzed Baeyer-Villiger--Type Oxidations Using Molecular Oxygen as the Oxidant |
|
|
465 | (1) |
|
Recent Progress in Asymmetric Wittig-Type Reactions |
|
|
466 | (3) |
|
Asymmetric Reformatsky Reactions |
|
|
469 | (1) |
|
Catalytic Asymmetric Wacker Cyclization |
|
|
470 | (1) |
|
Palladium-Catalyzed Asymmetric Alkenylation of Cyclic Olefins |
|
|
471 | (3) |
|
Intramolecular Enyne Cyclization |
|
|
474 | (1) |
|
Asymmetric Darzens Reaction |
|
|
475 | (1) |
|
Asymmetric Conjugate Addition |
|
|
476 | (5) |
|
Asymmetric Synthesis of Fluorinated Compounds |
|
|
481 | (3) |
|
New Concepts in Asymmetric Reaction |
|
|
484 | (15) |
|
Ti Catalysts from Self-Assembly Components |
|
|
484 | (2) |
|
|
|
486 | (1) |
|
Cooperative Asymmetric Catalysis |
|
|
486 | (6) |
|
Sterochemical Nonlinear Effects in Asymmetric Reaction |
|
|
492 | (2) |
|
|
|
494 | (2) |
|
Enantioselective Activation and Induced Chirality |
|
|
496 | (3) |
|
Chiral Amplification, Chiral Autocatalysis, and the Origin of Natural Chirality |
|
|
499 | (2) |
|
|
|
501 | (1) |
|
|
|
501 | (8) |
| Index |
|
509 | |