Enantioselective syntheses of α-amino acids from 10-sulfonamido-isobornyl esters and di-t-butyl azodicarboxylate

Von Oppolzer, Wolfgang; Moretti, Robert

doi:10.1016/S0040-4020(01)86059-2

Scientific article

English

Enantioselective syntheses of α-amino acids from 10-sulfonamido-isobornyl esters and di-t-butyl azodicarboxylate

ContributorsVon Oppolzer, Wolfgang; Moretti, Robert

Published inTetrahedron, vol. 44, no. 17, p. 5541-5552

Publication date1988

Abstract

Successive treatment of chiral esters 7 with LDA/Me₃SiCl and di-t-butyl azodicarboxylate/TiCl₄ and Ti(OiPr)₄ gave N,N-di-t-butoxycarbonylhydrazinoesters 11 which on deacylation, hydrogenolysis, transesterification and acidic hydrolysis furnished (2S)-α -amino acid hydrochlorides 13 in good overall yields, high enantiomeric purity and with efficient recovery of the alcohol auxiliary 4. Experimental evidence for the configuration and conformation of the intermediate O-silyl ketene acetals 1 is provided.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, MORETTI, Robert. Enantioselective syntheses of α-amino acids from 10-sulfonamido-isobornyl esters and di-t-butyl azodicarboxylate. In: Tetrahedron, 1988, vol. 44, n° 17, p. 5541–5552. doi: 10.1016/S0040-4020(01)86059-2

Article (Published version)

Identifiers

PID : unige:166724
DOI : 10.1016/S0040-4020(01)86059-2

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040402001860592

Journal ISSN0040-4020

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Enantioselective syntheses of α-amino acids from 10-sulfonamido-isobornyl esters and di-t-butyl azodicarboxylate

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