Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol

José M. Concellón, Pablo L. Bernad, R. Alvarez, A. Rodríguez, B. Baragaña

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

(2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2- ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2- epoxybutane.

Original languageEnglish
Pages (from-to)2863-2864
Number of pages2
JournalTetrahedron Letters
Volume40
Issue number14
DOIs
Publication statusPublished - 2 Apr 1999

Keywords

  • Chiral chloromethyl ketones
  • Diastereoselection
  • Reduction
  • β,γ-epoxy alcohols

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