SmI2-mediated 3-exo-trig cyclization of β,γ-unsaturated carbonyl compounds: diastereoselective synthesis of cyclopropanols

Org Lett. 2010 Sep 17;12(18):4082-5. doi: 10.1021/ol101666m.

Abstract

SmI(2)-mediated 3-exo-trig cyclizations of β,γ-unsaturated carbonyl compounds to generate cyclopropanols are not generally observed processes. The reported examples are limited to β,γ-unsaturated carbonyl compounds that possess ester groups conjugated with the alkene unit. The results of the current study show that this cyclization also occurs when other substitution patterns are present on the alkene moiety, affording (E)-cyclopropanols in good to excellent yields and in most cases with high degrees of diastereoselectivity.