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

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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.

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Romo, J. M., Gálvez, E., Nubiola, I., Romea, P., Urpí, F., & Kindred, M. (2013). Diastereoselective methyl orthoformate alkylations of chiral N-acylthiazolidinethiones catalyzed by nickel(II) complexes. Advanced Synthesis and Catalysis, 355(14–15), 2781–2786. https://doi.org/10.1002/adsc.201300521

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