Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

Naoya Sagawa, Haruka Sato, Seijiro Hosokawa

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.

Original languageEnglish
Pages (from-to)198-201
Number of pages4
JournalOrganic Letters
Volume19
Issue number1
DOIs
Publication statusPublished - 2017 Jan 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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