An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates?

Chemical Communications Pub Date: 2015-07-29 DOI: 10.1039/C5CC05549K

Abstract

A multicomponent reaction between imines, terminal alkynes, and isothiocyanates in the presence of a catalytic chiral copper–pybox complex proceeds enantioselectively to give enantiopure thiazolidine-2-imines (60–99% ee) via a highly regioselective intramolecular 5-exo-dig hydrothiolation reaction.

Graphical abstract: An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates
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