Enantioselective preparation of 3-substituted-4-pentenoic acids via the claisen rearrangement

Mark J. Kurth, Owen H W Decker

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94% diastereomeric excess. The overall chemical yields for 2 → 5 range from 51 to 78%. The aza-Claisen rearrangement (4 → 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity. Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.

Original languageEnglish (US)
Pages (from-to)5769-5775
Number of pages7
JournalJournal of Organic Chemistry
Volume50
Issue number26
StatePublished - 1985

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Acetals
Alkylating Agents
Hydrolysis
Acids
4-pentenoic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective preparation of 3-substituted-4-pentenoic acids via the claisen rearrangement. / Kurth, Mark J.; Decker, Owen H W.

In: Journal of Organic Chemistry, Vol. 50, No. 26, 1985, p. 5769-5775.

Research output: Contribution to journalArticle

Kurth, Mark J. ; Decker, Owen H W. / Enantioselective preparation of 3-substituted-4-pentenoic acids via the claisen rearrangement. In: Journal of Organic Chemistry. 1985 ; Vol. 50, No. 26. pp. 5769-5775.
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