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

Bui Thuy Trang, Cao Hai Thuong, Chu Chien Huu
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Authors

  • Bui Thuy Trang
  • Cao Hai Thuong
  • Chu Chien Huu

DOI:

https://doi.org/10.15625/2525-2321.2017-00450

Keywords:

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

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.

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References

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Published

28-04-2017

How to Cite

Trang, B. T., Thuong, C. H., & Huu, C. C. (2017). Carbohydrate as a chiral template: optical resolution of N-tert-butanesulfinamides. Vietnam Journal of Chemistry, 55(2), 231. https://doi.org/10.15625/2525-2321.2017-00450

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