Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Yujiro Hayashi, Shunsuke Toda

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3- syn - or 1,3- anti -dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B 0 is synthesized enantioselectively by using the present method as a key step.

Original languageEnglish
Pages (from-to)442-448
Number of pages7
JournalSynlett
Volume30
Issue number4
DOIs
Publication statusPublished - 2019

Keywords

  • Michael reaction
  • asymmetric synthesis
  • diastereoselective reaction
  • diphenylprolinol silyl ether
  • organocatalyst

ASJC Scopus subject areas

  • Organic Chemistry

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