A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.

Original languageEnglish
Pages (from-to)6629-6632
Number of pages4
JournalTetrahedron Letters
Volume28
Issue number52
DOIs
Publication statusPublished - Jan 1 1987
Externally publishedYes

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Oxazolidinones
Aldehydes
Derivatives
Dust
Zinc
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes. / Ito, Yoshio; Terashima, Shiro.

In: Tetrahedron Letters, Vol. 28, No. 52, 01.01.1987, p. 6629-6632.

Research output: Contribution to journalArticle

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