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

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.