Remote chirality control in 1,2-asymmetric induction: a remarkable difference between the meso- and (±)-isomers of dimethylglutaric hemialdehyde

Abstract

The Lewis acid mediated reaction of the meso-dimethylglutaric hemialdehyde (2) with pent-3-en–2-yltributyltin (1) gave the anti-Cram erythro isomer (4) predominantly, while the reaction of the (±)-isomer (3) produced the Cram erythro derivative (5) preferentially.