tailieunhanh - Carbohydrate as a chiral template: optical resolution of N-tert-butanesulfinamides
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. | Vietnam Journal of Chemistry, International Edition, 55(2): 231-235, 2017 DOI: Carbohydrate as a chiral template: optical resolution of N-tert-butanesulfinamides Bui Thuy Trang1, Cao Hai Thuong2*, Chu Chien Huu1 1 Millitary Intistute of Chemistry and Material, Hanoi, Vietnam 2 Department of Physics and Chemical Engineering, Le Quy Don Technical University, Hanoi, Vietnam Received 15 August 2016; Accepted for publication 11 April 2017 Abstract 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. 1. INTRODUCTION The past two decades have seen an explosion in interest in the synthesis and utility of molecules containing a stereogenic sulfur center [1]. Sulfoxides are found in a variety of natural products. They have also been employed as chiral auxiliaries in a range of reaction classes, and more recently as chiral ligands. Especially, chiral N-tert-butanesulfinamides are increasingly being utilized as versitale chiral nitrogen intermediates for the preparation of amines, aminoacids [2]. These amides are useful synthons for asymmetric synthesis of biogically active molecules [3]. Moreover, tert-butanesulfinamide is increasingly being applied across many additional research .
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