Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide

Sayaka Ishii, Katsuya Saito, Shigefumi Kuwahara, Masaru Enomoto

Research output: Contribution to journalArticlepeer-review

Abstract

A Lewis acid promoted nucleophilic addition of methallyltrimethylsilane to a chiral a-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of a-keto imides between Soai's and our cases might have affected the diastereofacial selectivity.

Original languageEnglish
Pages (from-to)488-492
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume85
Issue number3
DOIs
Publication statusPublished - 2021 Mar 1

Keywords

  • reversal of stereochemistry
  • α-hydroxycarboxylic acid
  • α-keto imide

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