Highly stereoselective reformatsky reactions of 3-(2-Bromopropionyl)-2-oxazolidone derivatives with various aldehydes

Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The Reformatsky reactions of 3-2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities. The highest 2,3-syn-diastereoselectivity (2,3-syn:2,3- anti=98:2) could be realized at -78°C by employing sterically crowded 3-(2- bromopropionyl)-4,4-dibutyl-5,5-pentamethylene-2-oxazolidone. While high 2,3-syn-3,4-syn-selectivity (2,3-syn-3,4-syn:2,3-syn-3,4-anti=94:6) was also accomplished by the reaction with di-2-phenylpropanal, application of this reaction to enantioselective synthesis of 2,3-syn-aldols was found to be unrewarding. The observed diastereoselectivities could be accounted for by the chelating transition state models.

Original languageEnglish
Pages (from-to)2821-2834
Number of pages14
JournalTetrahedron
Volume47
Issue number16-17
DOIs
Publication statusPublished - 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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