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	Foreword	V
	Message from the Editors	XXV
	List of Abbreviations	XXVII
	Named and Unnamed Reactions	XXXI
	List of Contributors	XXXIII
	Part I Chiral Auxiliaries in Asymmetric Synthesis
	Introductory Chapter David A. Evans, Günter Helmchen and Magnus Rüping	3
	Background	3
	Results	4
	Summary	7
	CV of David A. Evans	8
	CV of Günter Helmchen	8
	CV of Magnus Rüping	9
	Selected Publications	9
	Asymmetric Epoxidation of Pentadienols Reinhard Brückner	10
	Background	10
	Objective: Making Building Blocks for the Synthesis of 1,3,5,7,...-Polyols from Epoxyalcohols	11
	Results	12
	Asymmetric Epoxidation of a Conjugated Pentadienol	12
	Asymmetric Epoxidation of a Nonconjugated Pentadienol	13
	CV of Reinhard Brückner	15
	Selected Publications	16
	Asymmetric Synthesis using Sulfur–Nitrogen Reagents Franklin A. Davis	17
	Background	17
	Results	17
	Asymmetric Oxidations using N-Sulfonyloxaziridines	17
	Asymmetric Fluorination of Enolates with N-Fluoro-2,10-Camphorsultams	19
	Asymmetric Synthesis of Amine Derivatives using Enantiopure Sulfinimines (N-Sulfinyl Imines)	19
	Outlook	20
	CV of Franklin A. Davis	20
	Selected Publications	22
	Asymmetric Syntheses with SAMP-/RAMP-Hydrazones Dieter Enders and Wolfgang Bettray	23
	Background	23
	Strategy	24
	Results	25
	Application for the Synthesis of Natural Products	26
	Other Asymmetric Syntheses from the Enders Group	27
	Conclusions and Future Perspectives	27
	CV of Dieter Enders	27
	Selected Publications	28
	Asymmetric Allylation Reactions Reinhard W. Hoffmann	29
	Background	29
	Results	29
	Type (I) Allylmetallation of Aldehydes	29
	Second Generation Allylmetallation Reagents	31
	CV of Reinhard W. Hoffmann	32
	Selected Publications	33
	Carbohydrates as Chiral Auxiliaries Horst Kunz	34
	Introduction	34
	Results	34
	Carbohydrate Auxiliaries in Cycloaddition Reactions	34
	Conjugate Addition Reactions Directed by Carbohydrate Auxiliaries	35
	Glycosylamines in Stereoselective Synthesis	36
	Conclusions	38
	CV of Horst Kunz	38
	Selected Publications	38
	The Use of Chiral Oxazolines in early C–C Bond Forming Reactions Albert I. Meyers	39
	Background	39
	Results	40
	CV of Albert I. Meyers	41
	Selected Publications	41
	Asymmetric Synthesis of Amines and Amino Acids from Amines Shun-Ichi Murahashi and Yasushi Imada	42
	Background	42
	Strategy	43
	Results	43
	Diastereoselective Reactions of Nitrones	43
	Enantioselective Reactions of Nitrones	44
	Conclusions and Future Perspectives	46
	CV of Shun-Ichi Murahashi	46
	Selected Publications	47
	Part II Metal-catalyzed Asymmetric Synthesis
	Introductory Chapter Masakatsu Shibasaki and Shigeki Matsunaga	51
	Introduction	51
	Design of Asymmetric Metal Catalysis	52
	Future Prospects for Metal-catalyzed Asymmetric Synthesis	53
	CV of Masakatsu Shibasaki	54
	CV of Shigeki Matsunaga	54
	Selected Publications	55
	Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds Varinder Aggarwal	56
	Background	56
	Results	57
	Other Reactions of Sulfur Ylides from the Aggarwal Group	59
	Conclusions and Future Perspectives	59
	CV of Varinder Aggarwal	60
	Selected Publications	61
	Asymmetric Baeyer-Villiger Reactions Carsten Bolm	62
	Background	62
	Strategy	63
	Results	64
	Other Research Topics from the Bolm Group	65
	CV of Carsten Bolm	65
	Selected Publications	66
	Planar Chiral Ligands Based on [2.2]Paracyclophanes Stefan Bräse	67
	Background	67
	Strategy	68
	Results	69
	Application for the Synthesis of Natural Products	70
	Other Asymmetric Syntheses from the Bräse Group	70
	Conclusions and Future Perspectives	71
	CV of Stefan Bräse	71
	Selected Publications	71
	Asymmetric Syntheses of 3-(trans-2-Nitrocyclopropyl)alanine and 3-(trans-2-Aminocyclopropyl)alanine Armin de Meijere and Oleg V. Larionov	72
	Background	72
	Strategy and Results	73
	Outlook	75
	CV of Armin de Meijere	75
	CV of Oleg V. Larionov	76
	Selected Publications	76
	Copper-Bis(oxazoline) Catalyzed Synthesis of -Lactams - Enantioselective Reaction of Alkynes with Nitrones David A. Evans, Florian Kleinbeck and Magnus Rüping	77
	Background	77
	Results	78
	Summary	80
	CV of David A. Evans	81
	CV of Magnus Rüping	81
	CV of Florian Kleinbeck	81
	Selected Publications	81
	Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents Fernando López and Ben L. Feringa	83
	Background	83
	The First Catalytic Enantioselective Approaches	83
	Results	84
	Cu-catalyzed Enantioselective CA of Organozinc Reagents	84
	Highly Enantioselective Cu-catalyzed CA of Grignard Reagents	86
	Conclusion and Future Perspectives	87
	CV of Fernando López	87
	CV of Ben L. Feringa	88
	Selected Publications	88
	Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution Hans-Joachim Gais	90
	Introduction	90
	Strategy	91
	Results	91
	Application to the Synthesis of Natural Products	94
	Other Asymmetric Syntheses from the Gais Group	94
	Conclusion and Future Perspectives	94
	CV of Hans-Joachim Gais	94
	Selected Publications	95
	Asymmetric Cross-coupling Reactions Tamio Hayashi	97
	Background	97
	Results	97
	Asymmetric Cross-coupling of Secondary Alkyl Grignard Reagents	97
	Asymmetric Cross-Coupling Forming Axially Chiral Biaryls	99
	Conclusions and Future Perspectives	100
	CV of Tamio Hayashi	101
	Selected Publications	101
	Asymmetric Allylic Substitutions Günter Helmchen	102
	Background	102
	Results	103
	Pd-Catalyzed Allylic Substitutions	103
	Ir-Catalyzed Allylic Substitutions	104
	Application for the Synthesis of Biologically Active Compounds	104
	Other Asymmetric Syntheses from the Helmchen Group	105
	Conclusions and Future Perspectives	105
	CV of Günter Helmchen	105
	Selected Publications	106
	Asymmetric Homoaldol Reactions Dieter Hoppe	107
	Background	107
	Results	108
	Enantioselective Additions via Stereospecific Deprotonation	108
	Enantioselective Additions via (–)-Sparteine-mediated -Deprotonations	109
	Enantioselective -Deprotonations	110
	Synthetic Applications	110
	CV of Dieter Hoppe	111
	Selected Publications	111
	Asymmetric Vinylogous Mukaiyama Aldol Reaction Markus Kalesse and Jorma Hassfeld	112
	Introduction	112
	Results	112
	Conclusions and Further Perspectives	115
	CV of Markus Kalesse	116
	CV of Jorma Hassfeld	116
	Selected Publications	116
	Chiral Lewis Acid Catalysis in Aqueous Media Shu Kobayashi and Chikako Ogawa	117
	Background	117
	Results	117
	Water-compatible Lewis Acid	117
	Asymmetric Aldol Reactions	118
	Asymmetric Hydroxymethylation Reactions	119
	Asymmetric Mannich-type Reactions	120
	CV of Shu Kobayashi	121
	CV of Chikako Ogawa	121
	Selected Publications	122
	Asymmetric Epoxidation of Non-activated Olefins Kazuhiro Matsumoto and Tsutomu Katsuki	123
	Introduction	123
	Results	123
	Manganese(salen) Catalyst	123
	Ruthenium(salen) Catalyst	124
	Titanium(salalen) Catalyst	125
	Conclusion	126
	CV of Tsutomu Katsuki	127
	CV of Kazuhiro Matsumoto	127
	Selected Publications	127
	Chiral Carbonyl Lewis Acid Complexes in Asymmetric Syntheses Keiji Maruoka and Takashi Ooi	128
	Background	128
	Results	128
	Conclusions and Future Perspectives	131
	CV of Keiji Maruoka	131
	CV of Takashi Ooi	131
	Selected Publications	132
	ZACA Reaction: Zr-catalyzed Asymmetric Carboalumination of Alkenes Ei-ichi Negishi, Bo Liang, Tibor Novak and Ze Tan	133
	Background and Discovery	133
	Results	134
	ZACA–Pd-catalyzed Cross-coupling Tandem Processes
	for the Synthesis of Deoxypolypropionates and Related Compounds	134
	Synthesis of 2-Methyl- or 2-Ethyl-1-alkanols Not Readily
	Purifiable by Chromatography or Recrystallization	137
	CV of Ei-ichi Negishi	137
	Selected Publications	138
	Bisoxazolines – a Privileged Ligand Class for Asymmetric Catalysis Andreas Pfaltz	139
	Background	139
	Results	140
	Semicorrins	140
	C₂-Symmetric Bisoxazolines	140
	Boron-bridged Bisoxazolines	142
	Conclusion	142
	CV of Andreas Pfaltz	142
	Selected Publications	143
	Enantioselective Cycloaddition Reactions Catalyzed by Hydrogen Bonding Viresh H. Rawal and Avinash N. Thadani	144
	Background	144
	Strategy	146
	Results	146
	Application to Other Reactions	147
	Conclusions and Future Perspectives	147
	CV of Viresh H. Rawal	147
	Selected Publications	148
	Direct Catalytic Asymmetric Aldol-Tishchenko Reaction Masakatsu Shibasaki and Takashi Ohshima	149
	Background	149
	Strategy	150
	Results	150
	Mechanistic Studies	152
	Conclusions and Future Perspectives	153
	CV of Masakatsu Shibasaki	153
	CV of Takashi Ohshima	153
	Selected Publications	154
	Asymmetric Heck and other Palladium-catalyzed Reactions Lutz F. Tietze and Florian Lotz	155
	Background	155
	Enantioselective Heck Reactions with Allylsilanes as the Alkene Component	155
	CV of Lutz F. Tietze	159
	CV of Florian Lotz	159
	Selected Publications	160
	Asymmetric Catalysis with Chiral Acid Hisashi Yamamoto	161
	Background	161
	Results	162
	C₂ Symmetric Chiral Lewis Acid Catalysts	162
	Combined Acid Catalyst	162
	CV of Hisashi Yamamoto	165
	Selected Publications	165
	Part III Biocatalysis and Organocatalysis: Asymmetric Synthesis Inspired by Nature
	Introductory Chapter Benjamin List	169
	Introduction	169
	The Aldol Reaction as an Example	169
	Asymmetric Chemical Aldolizations	170
	Conclusions and Outlook	172
	CV of Benjamin List	173
	Selected Publications	173
	Enantioselective Photochemical Reactions Thorsten Bach	174
	Background	174
	Concept	175
	Results	175
	Perspectives	176
	CV of Thorsten Bach	178
	Selected Publications	178
	Asymmetric Catalysis via Dynamic Kinetic Resolution Jan-E. Bäckvall	179
	Background	179
	Combined Enzyme and Metal Catalysis for Efficient DKR	180
	Results	180
	Extension to DKR of Amines	182
	Conclusions and Future Perspectives	183
	CV of Jan-E. Bäckvall	183
	Selected Publications	183
	Catalytic Asymmetric Epoxidation of Enones and Related Compounds Albrecht Berkessel	185
	General	185
	Electrophilic Catalytic Epoxidation	186
	Nucleophilic Catalytic Epoxidation	186
	Conclusions and Future Perspectives	188
	CV of Albrecht Berkessel	188
	Selected Publications	189
	Kinetic Investigations of the Soai Autocatalytic Reaction Donna G. Blackmond	190
	Background	190
	Kinetic Studies using Reaction Calorimetry	191
	CV of Donna G. Blackmond	194
	Selected Publications	194
	Planar-chiral Heterocycles as Enantioselective Organocatalysts Gregory C. Fu	195
	Background and Design	195
	Applications	195
	Conclusions and Future Perspectives	199
	CV of Gregory C. Fu	199
	Selected Publications	199
	An Organocatalytic Approach to Optically Active Six-membered Rings Karl Anker Jørgensen	200
	Background	200
	Strategy	201
	Results	202
	Synthesis of - and -lactones	204
	Conclusions and Future Perspectives	204
	CV of Karl Anker Jørgensen	204
	Selected Publications	205
	Non-linear Effects in Asymmetric Catalysis Henri B. Kagan	206
	Background	206
	Enantiomerically Impure Chiral Auxiliaries	206
	Non-linear Effects	206
	Results	207
	Examples of Asymmetric Amplifications	207
	Kinetic Models	208
	Applications of Non-linear Effects	209
	Conclusion and Perspectives	209
	CV of Henri B. Kagan	209
	Selected Publications	210
	Asymmetric Organocatalysis Steven V. Ley	211
	Background	211
	Results	212
	Conclusions and Future Perspectives	216
	CV of Steven V. Ley	216
	Selected Publications	216
	Directed Evolution of Enzymes for Asymmetric Syntheses Manfred T. Reetz	217
	Background	217
	Strategy and Early Results	217
	Generalizing the Concept	219
	New Strategies	219
	Conclusions and Perspectives	220
	CV of Manfred T. Reetz	220
	Selected Publications	221
	Asymmetric Autocatalysis and Its Implications in the Origin of Chiral Homogeneity of Biomolecules	222
	Kenso Soai and Tsuneomi Kawasaki
	Background	222
	Results	223
	Chiral Amplification by Asymmetric Autocatalysis	223
	Asymmetric Autocatalysis as a Link Between the Origin of Chirality and Highly Enantioenriched Molecules	223
	Spontaneous Absolute Asymmetric Synthesis	224
	Conclusions and Future Perspectives	226
	CV of Kenso Soai	226
	CV of Tsuneomi Kawasaki	227
	Selected Publications	227
	Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase Chi-Huey Wong and William A. Greenberg	228
	Background	228
	Results	229
	Catalytic Mechanism	229
	Synthetic Applications	229
	Application to the Synthesis of Epothilones and Statins	230
	Conclusion	231
	CV of Chi-Huey Wong	232
	CV of William A. Greenberg	232
	Selected Publications	232
	Part IV Asymmetric Reactions in Total Synthesis
	Introductory Chapter K. C. Nicolaou and Paul G. Bulger	235
	Background	235
	Reactions	235
	Aldol	235
	Alkylation	237
	Diels–Alder	239
	Allylation	240
	Palladium-catalyzed Cross-coupling	241
	Epoxidation	244
	Dihydroxylation/aminohydroxylation	247
	Organocatalytic Reductions	248
	Metal-catalyzed Hydrogenations	248
	Enzymatic	250
	Conclusions	250
	CV of K. C. Nicolaou	251
	CV of Paul G. Bulger	251
	Selected Publications	252
	Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis Nicole Holub and Siegfried Blechert	254
	Background and Strategy	254
	Results	255
	Tetraponerines	255
	Trans-195A	256
	Lasubine II	256
	Astrophylline and Dendrochrysine	257
	Conclusions and Future Perspectives	258
	CV of Siegfried Blechert	259
	Selected Publications	259
	Asymmetric Synthesis of Biaryls by the “Lactone Method” Gerhard Bringmann, Tanja Gulder and Tobias A. M. Gulder	260
	Introduction	260
	The Basic Concept of the “Lactone Method”	260
	Application of the “Lactone Concept” to Natural Product Synthesis	261
	Conclusions and Further Perspectives	263
	CV of Gerhard Bringmann	263
	Selected Publications	264
	Asymmetric Synthesis of Merrilactone A	265
	Samuel J. Danishefsky
	Background	265
	Synthetic Strategy	265
	Synthesis of Merrilactone A	267
	CV of Samuel J. Danishefsky	269
	Selected Publications	270
	Asymmetric Synthesis of Cyclic Ketal and Spiroaminal-containing Natural Products Craig J. Forsyth	271
	Background	271
	Results	272
	Okadaic Acid – Three Spiroketalization Methods	272
	Additional Ketals via Double Intramolecular Hetero Michael Additions	273
	Synthesis of the Azaspiracid Spiroaminal	274
	Conclusion and Future Perspectives	275
	CV of Craig J. Forsyth	275
	Selected Publications	276
	Case Studies at the Metathesis/Asymmetric Synthesis Interface Alois Fürstner	277
	Background	277
	Results	277
	(–)-Gloeosporone	277
	(–)-Isooncinotine	279
	Conclusions and Future Perspectives	281
	CV of Alois Fürstner	281
	Selected Publications	281
	Asymmetric Synthesis of Amino Acids by Rhodium and Ruthenium Catalysis Jean Pierre Genet	282
	Introduction	282
	Asymmetric Hydrogenation Reactions	282
	Chiral Diphosphine Ligands and Diversity of Chiral Ru Catalysts	283
	Results	283
	Asymmetric Hydrogenation of Dehydroamino Acids	283
	Asymmetric Syntheses of -Amino -Hydroxy Acids (DKR)	284
	Asymmetric Syntheses of Natural Products	285
	Tandem-1,4 addition/Enantioselective Protonation Catalyzed by Rhodium	285
	Conclusions	286
	CV of Jean Pierre Genet	286
	Selected Publications	287
	Asymmetric Syntheses of Pheromones Kenji Mori	288
	Background	288
	Strategy and Results	288
	Derivation from Optically Active Starting Materials	289
	Enantiomer Separation	289
	Asymmetric Synthesis	290
	Conclusion and Future Perspective	292
	CV of Kenji Mori	292
	Selected Publications	292
	Total Synthesis of Polyketides Using Asymmetric Aldol Reactions Ian Paterson	293
	Background	293
	Results	294
	Stereocontrol in the Boron Aldol Reactions of Ketones	294
	Application to the Total Synthesis of Altohyrtin A (Spongistatin 1)	296
	Conclusions and Future Perspectives	296
	CV of Ian Paterson	296
	Selected Publications	298
	Asymmetric Synthesis on the Solid Phase Torben Leßmann and Herbert Waldmann	299
	Introduction	299
	Results	299
	Asymmetric Aldol Reactions	299
	Asymmetric Cycloadditions	300
	Asymmetric Epoxide Openings	302
	Other Reactions	302
	Conclusion	302
	CV of Herbert Waldmann	302
	CV of Torben Leßmann	303
	Selected Publications	303
	Part V Asymmetric Synthesis in Industry
	Introductory Chapter Herbert Hugl	307
	Background	307
	Industrial Production of Chiral Compounds	307
	Outlook	310
	CV of Herbert Hugl	310
	Selected Publications	310
	Industrial Application of Enantioselective Catalysis Hans-Ulrich Blaser	311
	The Potential of Enantioselective Catalysis	311
	Hurdles on the Way to an Industrial Process	311
	Catalyst Performance	312
	Availability and Cost of the Catalyst	312
	Development Time	313
	Selected Milestones in Industrial Application	313
	Conclusions and Future Perspectives	315
	CV of Hans-Ulrich Blaser	315
	Selected Publications	315
	Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant J. Brands, P. Pye and K. Rossen	316
	Background	316
	Results	317
	Bicyclic Acetal Approach	317
	Lactam Approach	318
	Conclusion	320
	CV of Karel M. Jos Brands	320
	CV of Philip Pye	320
	CV of Kai Rossen	320
	Selected Publications	321
	Combinatorial Methods in Asymmetric Syntheses Stefan Dahmen	322
	Background	322
	Results	322
	Ligand Screening	322
	Additive Screening	324
	Arylzinc Precursors	324
	CV of Stefan Dahmen	326
	Selected Publications	326
	Biocatalytic Production of Optically Active Amines Klaus Ditrich	327
	Background	327
	Results	327
	Conclusions and Future Perspectives	331
	CV of Klaus Ditrich	331
	Selected Publications	331
	The Monsanto L-Dopa Process William S. Knowles	332
	Background	332
	L-DOPA Process	332
	Other Industrial Applications	335
	Conclusions	335
	CV of William S. Knowles	335
	Selected Publications	336
	Asymmetric Hydrogenation through Metal–Ligand Bifunctional Catalysis Ryoji Noyori, Takeshi Ohkuma, Christian A. Sandoval and Kilian Muiz	337
	Background	337
	Strategy	337
	Results	337
	Catalytic Cycle	339
	CV of Ryoji Noyori	340
	Selected Publications	341
	Many Ways are Leading to Rome – Today’s Variety of Competing Synthetic Methods in Industry Andreas Job and Andreas Stolle	342
	Introduction	342
	Synthetic Concepts	343
	Biochemical Approach	344
	Catalytic Hydrogenation Approach	345
	Chiral Pool Synthesis	345
	Conclusion	346
	CV of Andreas Job	346
	CV of Andreas Stolle	346
	Selected Publications	347
	Author Index	349
	Subject Index	352

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