A NOVEL SYNTHETIC APPROACH TO α-AMINOPHOSPHINE SULFIDE STRUCTURES: THE FIRST ADDITION OF DIMETHYL-PHOSPHINE SULFIDE TO 3-THIAZOLINES

Abstract

The addition of dimethylphosphine sulfide to the C = N double bond of heterocycles is described for the first time. The alkylation of the phosphine sulfide derivative was achieved via a new synthetic approach for this P-nucleophile. Starting from the S-containing, 5-membered 3-thiazolines the corresponding N,S-heterocyclic 3-thiazolidin-4-yl-dimethylphosphine sulfides 3 were prepared. The use of a chiral 3-thiazoline allowed investigations about the diastereoselectivity of the addition reaction with the phosphine sulfide nucleophile via 1,3-induction.

Key Words:

• 4-Thiazolidinylphosphine sulfides
• Addition to the C = N double bond
• Diastereoselectivity
• Epimerization effect