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

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 i...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-06, Vol.82 (12), p.6426-6433
Main Authors: Kennington, Stuart C. D, Ferré, Mònica, Romo, Juan Manuel, Romea, Pedro, Urpí, Fèlix, Font-Bardia, Mercè
Format: Article
Language:English
Subjects:
Catalysis
Catàlisi
Chirality
Nickel
Níquel
Quiralitat
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00657