Asymmetric Synthesis of Substituted Homoallyl Alcohols, Halomethyl Tetrahydrofurans, and Chloro-amino Sulfones from Allyltitanium Sulfoximines and α-Hetero Aldehydes

Abstract

Asymmetric syntheses of the iodomethyl-substituted bicyclic tetrahydrofuran 22 and the chloro-amino sulfone 30 from the allylic sulfoximine 15 and the alpha-hetero aldehydes 2 and 23, respectively, are described. Further examples for the asymmetric synthesis of chloromethyl tetrahydrofurans and chloro-amino sulfones are given. The synthesis of 30 features as key step the stereoselective Cl-substitution of a hydroxy group under neighboring group participation by an aminosulfoxonium group which is converted to a sulfonyl group. [reaction: see text].