Carbohydrate as a chiral template: optical resolution of N-tert-butanesulfinamides

Bui Thuy Trang, Cao Hai Thuong, Chu Chien Huu


N-tert-butanesulfinamides, a class of amines bearing a sulfinyl group attached to nitrogen, exhibit pyramidal bonding where the non-bonded electron pair located at the sulfur atom acts as a fourth ligand. These compounds are configurationally sufficiently stable to be separated into R- and S- enantiomers. Enantiopure N-tert-butanesulfinamides are important auxiliaries in asymmetric synthesis, and some of them also have useful biological properties. In this paper, a new efficient strategy for enantioselective synthesis of N-tert-butanesulfinamides with very goods yields and excellent enantiomeric excess via the hydrolysis reaction of N-glycosidic bonds that were formed from D-ribose, under basic conditions was described.

Keywords. N-tert-butanesulfinamide, N-glycoside, D-ribose, enantiomer, asymmetric synthesis.


N-tert-butanesulfinamide, N-glycoside, D-ribose, enantiomer, asymmetric synthesis

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