Enantioselective Synthesis of Beta-Amino Acids

Name: Enantioselective Synthesis of Beta-Amino Acids
Price: 269.57 USD
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ISBN: 9780471467380

ISBN-10: 0471467383

ISBN-13: 9780471467380

Edition: 2nd 2005 (Revised)

Authors: Eusebio Juaristi, Vadim A. Soloshonok

List price: $343.95

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Interest in beta-amino acids has increased over the past several years. This book presents a discussion of the most important methods of for the synthesis of these compounds. This new edition is fully revised to reflect advances since 1996.

Book details

List price: $343.95
Edition: 2nd
Copyright year: 2005
Publisher: John Wiley & Sons, Incorporated
Publication date: 4/21/2005
Binding: Hardcover
Pages: 656
Size: 6.30" wide x 9.50" long x 1.40" tall
Weight: 2.2
Language: English



Contributors



Structural Types of Relevant -Amino Acid Targets




Introduction



Alkyl-substituted--amino Acids



Aryl-substituted--amino Acids



Olefinic and Alkynyl -amino Acids



ï¿½,-Diamino Acids



ï¿½-Hydroxy--amino Acids



-Amino-ï¿½-hydroxy Acids



Carbocyclic -Amino Acids



Heterocyclic -Amino Acids



References



-Amino Acids in Natural Products




Introduction



Natural Products Containing -Amino Acids Related to Proteinogenic a-Amino Acids



Natural Products Containing Aliphatic Hydroxy--amino Acids



Natural Products Containing Aliphatic -Amino Acids with Oxo Groups



Natural Products Containing Amino--amino Acids (Except -Lysine)



Alicyclic and Heterocyclic -Amino Acids



Natural Products Containing Unusual Aromatic -Amino Acids



Conclusions and Future Prospects



Dedication



Acknowledgement



References



Preparation of Enantiopure -Amino Acids by Homologation of ï¿½-Amino Acids




Introduction



The Arndt-Eistert Homologation



Homologation of Amino Acids with Concomitant -Lactam Formation



Homologation of Amino Acids Using Cyano Hydrins



References



Asymmetric Catalysis in the Enantioselective Synthesis of -Amino Acids




Introduction



Catalytic Asymmetric Conjugate Addition for the Preparation of -Aliphatic--Amino Acids



Asymmetric Mannich Reactions Catalyzed by Thiourea Derivatives for the Enantioselective Preparation of -Aryl--Amino Acids



References



Enantioselective Synthesis of Conformationally Constrained beta;-Amino Acids




General Introduction



Cycloalkane -Amino Acids



Alkyl Substituted -Amino Acids



Other methodologies



Acknowledgements



References



Catalytic Enantioselective Mannich Reactions




Introduction



Catalytic Enantioselective Mannich Reactions Using Chiral Lewis Acid Catalysts



Catalytic Asymmetric Mannich Reactions via Metal Enolates



Catalytic Asymmetric Reaction Using an Organocatalyst



Miscellaneous



References



Enantioselective Synthesis of -Amino Acids Via the Stereoselective Hydrogenation of -Aminoacrylic Acid Derivatives




Introduction



Recent Developments: Rhodium Complexes with Chiral Phosphorus Bidentate Ligands



Recent Developments: Rhodium Complexes with Chiral Phosphorus Monodentate Ligands



Recent Developments: Ruthenium Complexes with Chiral Phosphorus Bidentate Ligands



Acknowledgment



References



Asymmetric Synthesis of -Amino Acids by Enolate Additions to tert-Butanesulfinyl Imines




Introduction



Synthesis of N-tert-butanesulfinyl imines



Synthesis of N-sulfinyl protected -amino acids



The N-tert-butanesulfinyl protecting group



Synthetic Utility



Summary



References



Organocatalytic Approaches to Enantioenriched -Amino Acids( Fujie Tanaka and Carlos F. Barbas, III)



Introduction



Mannich-Type Reactions Using Aldehydes and ï¿½-Ethyl Glyoxylate



Mannich-type Reactions Using Aldehydes and Preformed Aldimines



Three-Component Mannich Reactions Using Aldehyde Donors



Proposed Mechanism for the L-Proline-Catalyzed Mannich Reactions



Transformation of the Product of the L-Proline-Catalyzed Mannich Reaction into - Amino Acid and -Lactams



One-pot Transformations via the L-Proline-Catalyzed Mannich Reactions Using Aldehydes as Nucleophiles



Mannich Reactions Using ï¿½,alpha;-Disubstituted Aldehydes or ï¿½-Imidoaldehyde for the Preparation of Highly Functionalyzed -Amino Acid Derivatives



Other Organocatalytic Reactions for the Preparation of Enantioenriched -Amino Acids



Summary



Experimental Procedures



References



Asymmetric Synthesis of Cyclic -Amino Acids via Cycloaddition Reactions




Introduction



General Strategies in Asymmetric Synthesis of Cyclic -Amino Acids



Cyclic -Amino Acids via Cycloaddition Reactions



Synthesis of cis- and trans-2-Aminocyclohexanecarboxylic Acid Derivatives via [4+2] Cycloaddition Reactions



Synthesis of -Proline Derivatives via [3+2] Cycloaddition Reactions



Synthesis of Constrained Six-Membered Ring ï¿½,ï¿½-Disubstituted -Amino Acid Derivatives via [4+2] Cycloaddition Reactions



Summary



References



Enantioselective Synthesis of Novel -Amino Acids




Introduction



Acyclic Amino Acids



Cyclic and conformationally constrained -amino acids



Experimental procedure for some select -amino acids



References



Asymmetric Synthesis of Phosphonic Analogs of -Amino Acids




Introduction



Enantioselective C-C Bond Forming Reactions



Enantioselective C-N Bond Forming Reactions



Enantioselective Asymmetric C-H Bond Forming Reactions



Miscellaneous



References



Asymmetric Synthesis of ï¿½-Substituted Amino Phosphonates and Phosphinates, and -Amino Sulfur Analogues




Introduction



Synthesis of ï¿½-Alkyl--Amino Phosphorus Derivatives



Synthesis of -Amino-ï¿½-Hydroxy Phosphonic and Phosphinic Acid Derivatives



Synthesis of -Amino-ï¿½-Halogenated Phosphonates



Synthesis of ï¿½,-Diamino Phosphonates and Phosphinates



-Amino-ï¿½-Substituted Phosphorus Derivatives with Peptide Bond Formation. -Amino-ï¿½-Substituted Phosphono- and Phosphinopeptides



-Amino Sulfur Analogues



Conclusion



Acknowledgments



References



Stereoselective Synthesis of Fluorine-Containing -Amino Acids




Introduction



Acyclic fluorinated ï¿½,-disubstituted -amino acids



Cyclic fluorinated ï¿½,-disubstituted -amino acids



ï¿½-Fluoroalkyl -amino acids



-Fluoroalkyl -amino acids



-Substituted-ï¿½,ï¿½-difluoro--amino acids



References



Enantioselective Synthesis of -Amino Acids Via Conjugate Addition to ï¿½,ï¿½-Unsaturated Carbonyl Compounds




Introduction



Diastereoselective Additions to Chiral Michael Acceptors



Additions of Chiral Ammonia Equivalents to Michael Acceptors



Methods Based on Asymmetric Catalysis



Experimental Section



References



Preparation of Enantiopure -Amino Acids Via Enantioselective Conjugate Addition




Introduction



Conjugate Addition of Alkyl or Aromatic Amines



Addition of Hydroxylamine to Enoates



Conjugate Addition of Azide



Conjugate Addition of Carbon-Nucleophiles



Conclusions



Acknowledgements



References



Biocatalytic Entry to Enantiomerically Pure -Amino Acids




Introduction



ï¿½-Substituted -Amino Acids



ï¿½,ï¿½-Disubstituted -Amino Acids



-Amino ï¿½-Hydroxy Acids



-Substituted -Amino Acids



Conclusion



References



Stereoselective Synthesis of -Amino Acids Via Radical Reactions




Introduction



Synthesis of Acyclic -Amino Acids



Synthesis of Cyclic -Amino Acids



Synthesis of -Lactams



References



Recent Advances in the Synthesis of ï¿½-Hydroxy--amino Acids and Their Use in the SAR Studies of Taxane Anticancer Agents




Introduction



Synthesis of Enantiopure ï¿½-Hydroxy--amino Acid Components of Taxane Anticancer Agents by -Lactam Synthon Method



New C-13 ï¿½-Hydroxy--amino Acid Residues and Their Significance in the Second Generation Taxoids



Taxoids