Synthesis of β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane and its application to asymmetric allylation

Abstract

Previously unknown tributyl-[(2-methylidene-4,4-diethoxy)butyl]stannane was prepared from diethyl acetal of 3-(bromomethyl)but-3-enal and was brought subsequently into a catalytic asymmetric Keck allylation of butanal in order to obtain optically active homoallylic alcohol. The use of activating additives [B(OBu)₃ and CF₃COOH] favors the process proceeding with high yields and enantioselectivity. An approach was suggested to the synthesis of С¹⁴–С²¹ fragments of amphidinolide Т applying tributyl[(2-methylidene-4,4-diethoxy)butyl]stannane in the key stage of building up the carbon scaffold.