Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Diastereoselective and Catalytic α-Alkylation of Chiral N-Acyl Thiazolidinethiones with Stable Carbocationic Salts

Diastereoselective and Catalytic α-Alkylation of Chiral N-Acyl Thiazolidinethiones with Stable Carbocationic Salts
Fèlix Urpí, Juan Manuel Romo, Mercè Font-Bardia, Pedro Romea, Stuart C. D. Kennington, Mònica Ferré
Direct nickel-catalyzed alkylation of chiral N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones using a commercially available nickel(II) complex, (Me3P)2NiCl2, has been developed for tropylium and trityl tetrafluoroborate salts. The reaction provides a single diastereomer of the corresponding adducts in good to high yields, which, in turn, can be easily converted into a wide array of enantiomerically pure compounds that are difficult to obtain by other asymmetric procedures.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00657

DOI: 10.1021/acs.joc.7b00657

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