Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives

Wei Chieh Cheng, Yannan Liu, Melissa Wong, Marilyn M. Olmstead, Kit Lam, Mark J. Kurth

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exomethyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereoselectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisoxazolinoproline amino acids.

Original languageEnglish (US)
Pages (from-to)5673-5677
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number16
DOIs
StatePublished - Aug 9 2002

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Derivatives
Amino Acids
Nitriles
Column chromatography
Oxides
Esters

ASJC Scopus subject areas

  • Organic Chemistry

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Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives. / Cheng, Wei Chieh; Liu, Yannan; Wong, Melissa; Olmstead, Marilyn M.; Lam, Kit; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 67, No. 16, 09.08.2002, p. 5673-5677.

Research output: Contribution to journalArticle

Cheng, Wei Chieh ; Liu, Yannan ; Wong, Melissa ; Olmstead, Marilyn M. ; Lam, Kit ; Kurth, Mark J. / Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 16. pp. 5673-5677.
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