Catalytic Asymmetric Intramolecular Cyclopropanation of α-Diazo-α-Silyl Acetate

Saori Inoue, Kotaro Nagatani, Haruka Tezuka, Yunosuke Hoshino, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of α-diazo-α-silyl acetates to form oxabicyclo[3.2.1]hexane, which proceeds with high yields and enantioselectivities, is described. The maximum enantiomeric excess observed was 96% ee and the absolute configuration of the products was elucidated. The counteranion of the Cu(I) catalyst was found to play a crucial role in determining the yields and enantioselectivities, with highly anionic counteranions improving both yields and enantioselectivities. Our previously reported model explains the enantiofacial selectivity of the reacting alkene.

Original languageEnglish
Article numberst-2016-u0854-l
Pages (from-to)1065-1070
Number of pages6
JournalSynlett
Volume28
Issue number9
DOIs
Publication statusPublished - 2017 Jun 1

Keywords

  • asymmetric catalysis
  • cyclopropanation
  • diazo compounds
  • enantioselectivity
  • lactones

ASJC Scopus subject areas

  • Organic Chemistry

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