Reactions of the vicinal dianion of di-(-)-menthyl succinate with carbonyl compounds and benzyl bromide

Abstract

The diastereoselective reaction of the vicinal dianion, generated from di-(−)-menthyl succinate, with electrophiles, i.e. symmetrical ketones, aldehydes, and benzyl bromide was examined. The reactions with ketones and benzyl bromide gave products in good yields, however, with poor diastereoselectivities. The reaction with aldehydes in the presence of ZnCl 2 preferably gave the anti-aldol adducts, which subsequently led to cis-paraconic esters again with moderate diastereoselectivity.