Diastereoselective methyl orthoformate alkylations of chiral N-acylthiazolidinethiones catalyzed by nickel(II) complexes

Abstract

The completely diastereoselective silyl triflate-mediated methyl orthoformate alkylation of chiral N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones catalyzed by commercially available nickel(II) complexes is reported. The simple experimental procedure requires 2.5-5 mol% of bis(phosphine)nickel dichloride [(R3P)2NiCl2] complexes, proceeds under very mild conditions, and covers a wide array of acyl groups. Furthermore, it can potentially be expanded to different electrophiles. © 2013 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.