Journal ArticleDOI
Alpha-imino esters: versatile substrates for the catalytic, asymmetric synthesis of alpha- and beta-amino acids and beta-lactams.
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TLDR
The catalytic asymmetric addition of organic nucleophiles to α-imino esters has emerged as one of the most promising and intensely investigated routes to optically enriched α- andβ-amino acid derivatives and β-lactams.Abstract:
The catalytic asymmetric addition of organic nucleophiles to alpha-imino esters has emerged as one of the most promising and intensely investigated routes to optically enriched alpha- and beta-amino acid derivatives and beta-lactams. The importance of alpha-imino esters stems not only from the vast appeal of the potential product classes,(1) but also from their remarkable reactivity as highly electrophilic imines. With each passing year, the number of publications concerning the asymmetric alkylation of imino esters grows significantly. The asymmetric alkylation of imines(2) and N,O-acetals has been in itself a subject of intense interest.(3) In this Account, we wish to illustrate our contribution to this timely field, as well as to highlight the seminal contributions of others.read more
Citations
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Journal ArticleDOI
Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
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Catalytic Asymmetric Synthesis of α-Amino Acids
Carmen Nájera,José M. Sansano +1 more
Journal ArticleDOI
Asymmetric Synthesis of Tertiary Alcohols and α-Tertiary Amines via Cu-Catalyzed C−C Bond Formation to Ketones and Ketimines
Masakatsu Shibasaki,Motomu Kanai +1 more
TL;DR: Asymmetric catalysts that promote C-C bond-formation to ketones and ketimines should have high catalyst activity and enantioselectivity for synthetically more efficient addition to tetrasubstituted carbon synthesis.
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β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products
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Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis
TL;DR: This paper presents Kinetic Resolution of Alcohols and Amines and Catalysis on Sequentially-Linked Columns, a large-scale study of single-crystal catalysis, which aims at determining the carrier and removal status of Amines in response to alcohol.
References
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Journal ArticleDOI
The Direct Catalytic Asymmetric Three-Component Mannich Reaction
Benjamin List,Benjamin List +1 more
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The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of β-Lactams
TL;DR: Practical methodology for the catalytic, asymmetric synthesis of beta-lactams resulting from the development of a catalyzed reaction of ketenes (or their derived zwitterionic enolates) and imines is reported.
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A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids
TL;DR: In reactions involving ketone donors where diastereoisomeric products could be formed, two adjacent stereogenic centers were created simultaneously upon carbon−carbon bond formation with complete syn-stereocontrol.
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Enantioselective Addition of Enol Silyl Ethers to Imines Catalyzed by Palladium Complexes: A Novel Way to Optically Active Acylalanine Derivatives
Journal ArticleDOI
Catalytic, Enantioselective Alkylation of α-Imino Esters Using Late Transition Metal Phosphine Complexes as Catalysts
TL;DR: A means to alkylate R-imino esters enantioselectively in up to 98% ee and in high chemical yields with enol silanes using chiral catalytic late transition metal phosphine complexes selected from Ag(I), Cu(I, Ni(II), and Pd(II) (eq 2).