Quinine-catalyzed asymmetric domino Mannich-cyclization reactions of 3-isothiocyanato oxindoles with imines for the synthesis of spirocyclic oxindoles

摘要

A range of structurally diverse chiral spiro[imidazolidine-2-thione-4,3'-oxindole] compounds could be obtained via a domino Mannich-cyclization reaction of 3-isothiocyanato oxindoles and imines with commercial quinine as catalyst under mild conditions. The protocol is significantly characterized by simple process, easily available catalyst, high reactivity, low catalyst loading (1 mol %), and good to excellent diastereo- and enantioselectivity (up to>99:1 dr and 97% ee). A plausible dual activation working model was tentatively proposed to account for the stereochemistry of the domino Mannich-cyclization process. (C) 2014 Elsevier Ltd. All rights reserved.