Catalytic tandem C-C bond formation/cleavage of cyclopropene for allylzincation of aldehydes or aldimine using organozinc reagents

Takeo Nakano, Kohei Endo, Yutaka Ukaji

Research output: Contribution to journalArticlepeer-review

Abstract

The tandem allylation of aldehydes or an aldimine with allylzinc intermediates derived from organozinc reagents and cyclopropenes is described. The present three-component reaction involves carbozincation of cyclopropene and sequential cleavage of a cyclopropylzinc intermediate in situ without a transition-metal catalyst. The allylzinc intermediates generated in situ, which is an α,β-unsaturated acylanion equivalent, gave the corresponding homoallylic alcohols or amine in good yields.

Original languageEnglish
Pages (from-to)1418-1421
Number of pages4
JournalOrganic letters
Volume16
Issue number5
DOIs
Publication statusPublished - Mar 7 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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