Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective tandem Mannich-Michael reaction with Danishefsky's diene in the presence of Lewis acids. The temperature, catalyst and solvent dependence of the product ratio is described. Under zinc iodide-catalysed conditions in acetonitrile at −20°C, double stereodifferentiation using (R)-2,3-di-O-benzylglyceraldehyde (S)-N-α-(methylbenzyl)imine as starting material was successful and the reaction occurred with good yield and complete diastereoselectivity.This work was made possible by the generous financial support of the Dirección General de Investigación Científica y Técnica, project number PB94-0098. R. B. would like to express his gratitude to the Ministerio de Educación y Cultura for a grant.Peer reviewe