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

The Journal of Organic Chemistry
Stuart C D KenningtonMercè Font-Bardia

Abstract

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.

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Citations

Apr 29, 2021·The Journal of Organic Chemistry·Natalia PrusinowskaMarcin Kwit
Dec 23, 2020·The Journal of Organic Chemistry·Bartosz StasiakMarcin Kwit
Oct 27, 2021·Organic Letters·Marina Pérez-PalauMercè Font-Bardia

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