Classics in Stereoselective Synthesis

Classics in Stereoselective Synthesis

By: Lisbet Kvaerno (author), Erick M. Carreira (author)Paperback

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Description

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

About Author

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.

Contents

MACROCYCLIC STEREOCONTROL. Introduction. Background. Conformational Control in Medium-Sized Rings. Asymmetric Synthesis with Medium-Sized Rings. Case Studies in Natural Products Total Synthesis. Macrocyclic Stereocontrol in Cyclic Peptides. Appendix: Macrocycle Formation. CARBONYL ADITION REACTIONS. Introduction. Non-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects. 1,2-Asymmetric Induction Predicated on Chelation Control. 1,3-Asymmetric Induction from CBeta Stereogenic Centers. Asymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction). Catalytic Enantioselective Carbonyl Additions of Arganozinc Species. Enantioselective Ketone Reduction. Enzymatic Reduction of Ketones. Enantioselective Formation of Cyanohydrins. Enantioselective Alkyne Additions. Asymmetric Carbonyl-Ene Reactions. ALPHA-FUNCTIONALIZATIONS OF ENOLATES. Introduction. Diastereoselective Alpha-Alkylations of Chiral Enolates. Heteroatom-Substituted Enolates. Asymmetric Enolate Alkylations Using Chiral Auxiliaries. Enantioselective Enolate Alkylations. Alpha-Hydroxylations of Enolates. Alpha-Halogenations of Enolates. ALDOL REACTIONS. Introduction. Chiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller Groups. Substrate Control with Chiral Carbonyl Compounds. Catalytic Enantioselective Aldol Reactions. ALLYLATIONS OF C=O BONDS. Introduction. Reactivity of Allylmetal Reagents. Boronate Additions. Enantioselective Additions of Optically Active Allylic Boron Reagents. Diastereoselecive Allylations with Chiral Boron Reagents. Mechanistic Aspects - Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to Aldehydes. Chelation Control in the Allylation of Alpha- and Beta-Alkoxy Aldehydes. Allylchromium Reagents. Diastereoselective Allylations with Chiral Silanes and Stannanes. Catalytic Asymmetric Allylations. CHIRAL ACETALS. Introduction. Diastereoselective Reactions of Chiral Acetals. Glycosylations. Spiroketals in Natural Product Synthesis. ALKENE HYDROBORATION. Introduction. Hydroborations with Acyclic Stereocontrol. Metal-Catalyzed Hydroborations. Asymmetric Hydroborations with Chiral Boranes. Catalytic Asymmetric Hydroboration, Hydrosilylation, and Hydroalumination. REDUCTIONS OF OLEFINS. Introduction. Diastereoselective Olefin Reductions by Catalytic Hydrogenation. Alternative Methods for Diastereoselective Olefin Reductions. Catalytic Asymmetric Olefin Hydrogenations. OXIDATIONS OF OLEFINS. Introduction. Diastereoselective Epoxidations. Enantioselective Epoxidations. Asymmetric Ring-Opening of Epoxides. Synthesis of Aziridines. Iodolactonizations and Other Olefin Cyclizations Induced by Electrophiles. Diastereoselective Dihydroxylations of Olefins. Enantioselective Dihydroxylations of Olefins. Enantioselective Aminohydroxylation of Olefins. AMINO ACIDS. Introduction. Enantioselective Hydrogenations of Alpha, Beta-Didehydroamino Acids. Enolate Alkylations in the Presence of Chiral Auxiliaries. Alkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer Catalysts. Enolate Aminations. Enzymatic Syntheses of Alpha-Amino Acids. Catalytic Asymmetric Strecker Reactions. ADDITIONS TO C=N BONDS. Introduction. Substrate-Controlled Diastereoselective Additions to C=N Bonds. Additions to Imine Derivatives Bearing N-Bound Auxiliaries. Formation of Beta-Lactams Through Staudinger Reactions. Intramolecular Diastereoselective Iminium Ion Cyclizations. Pictet-Spengler Reactions. Catalytic Asymmetric Reductions of Imines and Imine Derivatives. Catalytic Enantioselective Mannich and Mannich-Type Reactions. Enantioselective Additions of Carbon Nucleophiles to C=N Bonds. CONJUGATE ADDITIONS. Introduction. Diastereoselective Conjugate Additions. Diastereoselective Conjugate Additions with Use of Chiral Auxiliaries. Enantioselective Conjugate Additions of Enolates and other Stabilized Carbon Nucleophiles. Enantioselective Conjugate Additions of Organometallic Species. Enantioselective Conjugate Additions of Radicals. Enantioselective Conjugate Additions of Heteroatom Nucleophiles. Conjugate Reductions. Catalytic Enantioselective Stetter Reactions. CHIRAL CARBONIONS. Introduction. Organolithium Reagents by Transmetalation of Organostannanes. Carbanions by Reductive Methods. Chiral Carbanions by Deprotonation. Sulfoxide- and Phosphorus-Stabilized Carbanions. Metal-Mediated Enantioselective Olefin Functionalizations. METAL-CATALYZED ALLYLATIONS. Introduction. Diastereoselective Palladium-Catalyzed Allylation Reactions. Enantioselective Palladium-Catalyzed Allylation Reactions. Iridium-Catalyzed Enantioselective Allylation Reactions. Copper-Catalyzed SN2' Allylation Reactions. Enantioselective Allylation Reactions Catalyzed by Other Transition Metals. Asymmetric Ring-Opening Reactions of Unsaturated Heterocycles. CYCLOPROPANATIONS AND C-H INSERTION REACTIONS. Introduction. Diastereoselective Cyclopropanations with Carbenoids Generated from Diazoalkanes. Enantioselective Dyclopropanations with Carbenoids Generated from Diazoalkanes. Diastereoselective Simmons-Smith Cyclopropanations. Enantioselective Simmons-Smith Cyclopropanations. Alternative Classes Cyclopropanations. Diastereoselective C-H Bonds. SIGMATROPIC REARRANGEMENTS. Introduction. Claisen and Claisen-Type [3,3]-Sigmatropic Rearrangements. Cope and Cope-Type [3,3]-Sigmatropic Rearrangements. [2,3]-Sigmatropic Rearrangements. Ene Reactions. Nazarov Cyclizations. DIELS-ALDER AND HETERO-DIELS-ALDER REACTIONS. Introduction. Diastereoselective Intermolecular Diels-Alder Reactions. Diastereoselective Intramolecular Diels-Alder Reactions. Diastereoselective Diels-Alder Reactions Using Chiral Auxiliaries. Catalytic Enantioselective Diels-Alder Reactions. Diastereoselective Hetero-Diels-Alder Reactions. Enantioselective Hetero-Diels-Alder Reactions. [3+2]- AND [2+2]-CYCLOADDITION REACTIONS. Introduction. Substrate-Controlled Diastereoselective [1,3]-Dipolar Cycloadditions. Diastereoselective [1,3]-Dipolar Cycloadditions Using Chiral Auxiliaries. Catalytic Enantioselective [1,3]-Dipolar Cycloadditions. [3+2]-Cycloadditions with Trimethylenemethane Equivalents. Ketene Cycloadditions. Photochemical [2+2]-Cycloadditions.

Product Details

  • ISBN13: 9783527299669
  • Format: Paperback
  • Number Of Pages: 651
  • ID: 9783527299669
  • weight: 1446
  • ISBN10: 3527299661

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