Classics in Stereoselective Synthesis

Erick M. Carreira, born in La Habana, Cuba, obtained a B.S. degree in 1984 from the University of Illinois at Urbana Champaign under the supervision of Scott E. Denmark, and a PhD in 1990 from Harvard University under the supervision of David A. Evans. After carrying out postdoctoral work with Peter Dervan at the California Institute of Technology through mid-1992, he joined the faculty at the same institution as an assistant professor of chemistry and was promoted to full professor in 1997. In 1998, he moved to the Laboratory of Organic Chemistry at the ETH-Zurich, Switzerland. He has over 180 research publications and numerous patents to his name. He is the recipient of, among others, the American Chemical Society Award in Pure Chemistry the Nobel Laureate Signature Award, and he has held the David and Lucile Packard Foundation Fellowship in Science and Engineering as well as the Tetrahedron Chair Prize. Professor Carreira's research program is focused on the four interrelated areas of organic synthesis: catalysis, methodology, natural products synthesis, and bioorganic chemistry. Lisbet Kvaerno, born in Denmark, received her M.Sc. in chemistry from the University of Copenhagen under Prof. Jesper Wengel. She obtained her PhD in 2004 after working in total synthesis at the Technical University of Denmark under Prof. David Tanner and in medicinal chemistry at the ETH Zurich supervised by Prof. Erick M. Carreira. As a postdoctoral fellow in the research group of Prof. David A. Evans at Harvard University, she completed the total synthesis of the marine natural product (+)-azaspiracid. After a brief period as an independent junior group leader at the Max Planck Institute of Coal Research in Muelheim, Germany, she joined Lundbeck in Copenhagen as a process chemist in the late summer of 2008.

"The book provides a collection of classic methods for stereoselective synthesis that have been developed over the past two decades - methods that should be at the command of every modern practitioner of synthetic organic chemistry." (Booknews, 1 April 2011)"The coherent appearance of all illustrations, multiple insertions of important concepts in boxes separate from the main text as well as many enlightening citations from prominent chemists and classic papers make this book unique and very enjoyable to read." (Chemistry World, November 2009)"Carreira and Kvaerno have provided a magnificent book that will be useful to students, instructors, and practicing chemists in industry and academia alike." (Angewandte Chemie, August 2009)

• MACROCYCLIC STEREOCONTROLIntroductionBackgroundConformational Control in Medium-Sized RingsAsymmetric Synthesis with Medium-Sized RingsCase Studies in Natural Products Total SynthesisMacrocyclic Stereocontrol in Cyclic PeptidesAppendix: Macrocycle FormationCARBONYL ADITION REACTIONSIntroductionNon-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects1,2-Asymmetric Induction Predicated on Chelation Control1,3-Asymmetric Induction from CBeta Stereogenic CentersAsymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction)Catalytic Enantioselective Carbonyl Additions of Arganozinc SpeciesEnantioselective Ketone ReductionEnzymatic Reduction of KetonesEnantioselective Formation of CyanohydrinsEnantioselective Alkyne AdditionsAsymmetric Carbonyl-Ene ReactionsALPHA-FUNCTIONALIZATIONS OF ENOLATESIntroductionDiastereoselective Alpha-Alkylations of Chiral EnolatesHeteroatom-Substituted EnolatesAsymmetric Enolate Alkylations Using Chiral AuxiliariesEnantioselective Enolate AlkylationsAlpha-Hydroxylations of EnolatesAlpha-Halogenations of EnolatesALDOL REACTIONSIntroductionChiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller GroupsSubstrate Control with Chiral Carbonyl CompoundsCatalytic Enantioselective Aldol ReactionsALLYLATIONS OF C=O BONDSIntroductionReactivity of Allylmetal ReagentsBoronate AdditionsEnantioselective Additions of Optically Active Allylic Boron ReagentsDiastereoselecive Allylations with Chiral Boron ReagentsMechanistic Aspects -Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to AldehydesChelation Control in the Allylation of Alpha- and Beta-Alkoxy AldehydesAllylchromium ReagentsDiastereoselective Allylations with Chiral Silanes and StannanesCatalytic Asymmetric AllylationsCHIRAL ACETALSIntroductionDiastereoselective Reactions of Chiral AcetalsGlycosylationsSpiroketals in Natural Product SynthesisALKENE HYDROBORATIONIntroductionHydroborations with Acyclic StereocontrolMetal-Catalyzed HydroborationsAsymmetric Hydroborations with Chiral BoranesCatalytic Asymmetric Hydroboration, Hydrosilylation, and HydroaluminationREDUCTIONS OF OLEFINSIntroductionDiastereoselective Olefin Reductions by Catalytic HydrogenationAlternative Methods for Diastereoselective Olefin ReductionsCatalytic Asymmetric Olefin HydrogenationsOXIDATIONS OF OLEFINSIntroductionDiastereoselective EpoxidationsEnantioselective EpoxidationsAsymmetric Ring-Opening of EpoxidesSynthesis of AziridinesIodolactonizations and Other Olefin Cyclizations Induced by ElectrophilesDiastereoselective Dihydroxylations of OlefinsEnantioselective Dihydroxylations of OlefinsEnantioselective Aminohydroxylation of OlefinsAMINO ACIDSIntroductionEnantioselective Hydrogenations of Alpha, Beta-Didehydroamino AcidsEnolate Alkylations in the Presence of Chiral AuxiliariesAlkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer CatalystsEnolate AminationsEnzymatic Syntheses of Alpha-Amino AcidsCatalytic Asymmetric Strecker ReactionsADDITIONS TO C=N BONDSIntroductionSubstrate-Controlled Diastereoselective Additions to C=N BondsAdditions to Imine Derivatives Bearing N-Bound AuxiliariesFormation of Beta-Lactams Through Staudinger ReactionsIntramolecular Diastereoselective Iminium Ion CyclizationsPictet-Spengler ReactionsCatalytic Asymmetric Reductions of Imines and Imine DerivativesCatalytic Enantioselective Mannich and Mannich-Type ReactionsEnantioselective Additions of Carbon Nucleophiles to C=N BondsCONJUGATE ADDITIONSIntroductionDiastereoselective Conjugate AdditionsDiastereoselective Conjugate Additions with Use of Chiral AuxiliariesEnantioselective Conjugate Additions of Enolates and other Stabilized Carbon NucleophilesEnantioselective Conjugate Additions of Organometallic SpeciesEnantioselective Conjugate Additions of RadicalsEnantioselective Conjugate Additions of Heteroatom NucleophilesConjugate ReductionsCatalytic Enantioselective Stetter ReactionsCHIRAL CARBONIONSIntroductionOrganolithium Reagents by Transmetalation of OrganostannanesCarbanions by Reductive MethodsChiral Carbanions by DeprotonationSulfoxide- and Phosphorus-Stabilized CarbanionsMetal-Mediated Enantioselective Olefin FunctionalizationsMETAL-CATALYZED ALLYLATIONSIntroductionDiastereoselective Palladium-Catalyzed Allylation ReactionsEnantioselective Palladium-Catalyzed Allylation ReactionsIridium-Catalyzed Enantioselective Allylation ReactionsCopper-Catalyzed SN2' Allylation ReactionsEnantioselective Allylation Reactions Catalyzed by Other Transition MetalsAsymmetric Ring-Opening Reactions of Unsaturated HeterocyclesCYCLOPROPANATIONS AND C-H INSERTION REACTIONSIntroductionDiastereoselective Cyclopropanations with Carbenoids Generated from DiazoalkanesEnantioselective Dyclopropanations with Carbenoids Generated from DiazoalkanesDiastereoselective Simmons-Smith CyclopropanationsEnantioselective Simmons-Smith CyclopropanationsAlternative Classes CyclopropanationsDiastereoselective C-H BondsSIGMATROPIC REARRANGEMENTSIntroductionClaisen and Claisen-Type [3,3]-Sigmatropic RearrangementsCope and Cope-Type [3,3]-Sigmatropic Rearrangements[2,3]-Sigmatropic RearrangementsEne ReactionsNazarov CyclizationsDIELS-ALDER AND HETERO-DIELS-ALDER REACTIONSIntroductionDiastereoselective Intermolecular Diels-Alder ReactionsDiastereoselective Intramolecular Diels-Alder ReactionsDiastereoselective Diels-Alder Reactions Using Chiral AuxiliariesCatalytic Enantioselective Diels-Alder ReactionsDiastereoselective Hetero-Diels-Alder ReactionsEnantioselective Hetero-Diels-Alder Reactions[3+2]- AND [2+2]-CYCLOADDITION REACTIONSIntroductionSubstrate-Controlled Diastereoselective [1,3]-Dipolar CycloadditionsDiastereoselective [1,3]-Dipolar Cycloadditions Using Chiral AuxiliariesCatalytic Enantioselective [1,3]-Dipolar Cycloadditions[3+2]-Cycloadditions with Trimethylenemethane EquivalentsKetene CycloadditionsPhotochemical [2+2]-Cycloadditions