Stereochemistry of Addition of Allyl Grignard Reagents to (R)-(+)-Pulegone and Other α,β-Ethylenic Ketones

Article abstract of DOI:10.1021/jo00240a014

The 1,2-addition of allyl, crotyl, and 2-methyl-2-butenyl Grignard reagents to (R)-(+)-pulegone is regio- and stereoselective.In contrast 3-penten-2-yl and 3-methyl-2-butenyl Grignard reagents undergo 1,2- and 1,4-additions.A "compact approach" stabilized by orbital interaction is the proposed mechanism.A further confirmation was obtained with acyclic enones.