Stereodivergent access to cis- and trans-3,5-disubstituted 1,4-thiazane 1-oxides by cyclization of homochiral β-amino sulfoxides and sulfones. The preparation of isomeric ant venom alkaloids

Abstract

Intramolecular conjugate additions of homochiral (E)-1-alkenyl 2-aminoalkyl sulfoxides and sulfones were investigated. The relative position of the 3,5-substituents of the resulting 1,4-thiazane oxides was found to be dependent on the oxidation state of the sulfur atom, demonstrating a simple and highly stereodivergent synthetic protocol. Selected cis- and trans-3,5-disubstituted 1,4-thiazane dioxides were converted to cis- and trans-2,5-disubstituted pyrrolidines, known ant venom alkaloids.