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 α-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of α-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 Feb 24

Keywords

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

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide'. Together they form a unique fingerprint.

Cite this