Enantioselective Syntheses of α-Amino Acids from 10-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate. Preliminary Communication

Von Oppolzer, Wolfgang; Moretti, Robert

doi:10.1002/hlca.19860690819

Scientific article

English

Enantioselective Syntheses of α-Amino Acids from 10-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate. Preliminary Communication

ContributorsVon Oppolzer, Wolfgang; Moretti, Robert

Published inHelvetica chimica acta, vol. 69, no. 8, p. 1923-1926

Publication date1986-12-10

Abstract

Succesive treatment of chiral esters 1 with LiN(i-Pr)2/Me3SiCl and di(tert-butyl) azodicarboxylate/TiCl4/Ti(i-PrO)4 gave N,N′ -di[(tert-butoxy)carbonyl]hydrazino esters 9 which on deacylation, hydrogenolysis, transesterification, and acidic hydrolysis furnished (2S)-α-amino acids 6 in high enantiomeric purity with efficient recovery of the auxiliary alcohol 7.

NotePresented (W.O.) in part at the IASOC II Meeting, Ischia, May 1986. At the same occasion, C. Gennari presented an independent approach to amino acids via asymmetric addition of ephedrine-derived ketene silyl acetals to di(tert-butyl) azodicarboxylate.

Affiliation

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-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate. Preliminary Communication. In: Helvetica chimica acta, 1986, vol. 69, n° 8, p. 1923–1926. doi: 10.1002/hlca.19860690819

Article (Published version)

Identifiers

PID : unige:156109
DOI : 10.1002/hlca.19860690819

Commercial URLhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19860690819

ISSN of the journal0018-019X

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Enantioselective Syntheses of α-Amino Acids from 10-(Aminosulfonyl)-2-bornyl Esters and Di(tert-butyl) Azodicarboxylate. Preliminary Communication

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