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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


(a) Pellissier H. Use of chiral sulfoxides in asymmetric synthesis, Tetrahedron., 62, 5559-5601 (2006). (b) Fernández I., Khiar N. Recent Developments in the Synthesis and Utilization of Chiral Sulfoxides, Chem. Rev., 103, 3651-3706 (2003).

M. C. Carreno, Chem. Rev. Applications of Sulfoxides to Asymmetric Synthesis of Biologically Active Compounds., 95, 1717-1760 (1995).

(a) P. Zhou, B.-C. Chen, F. A. Davis. Advances in Sulfur Chemistry, Vol. 2 (Eds.: C. M. Raynor), JAI Press, Stamford, CT, 249-282 (2000); (b) F. A. Davis, P. Zhou, B.-C. Chen. Asymmetric synthesis of amino acids using sulfinimines (thiooxime S-oxides), Chem. Soc. Rev., 27, 13-18 (1998); (c) F. A. Davis, R. E. Reddy. Phosphorus, Sulfur, Silicon Relat. Elem., 120/121, 291-303 (1997).

Liu G., Cogan D. A., Ellman J. A. Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines, J. Am. Chem. Soc., 119, 9913-9914 (1997).

Cogan D. A., Liu G., Kim K., Backes B. J., Ellman, J. A. Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines, J. Am. Chem. Soc., 120, 8011-8019 (1998).

Liao J., Sun X., Cui X., Yu K., Zhu J., Deng J. Facile Optical Resolution of tert-Butanethiosulfinate by Molecular Complexation with (R)-BINOL and Study of Chiral Discrimination of the Diastereomeric Complexes, Chem. Eur. J., 9, 2611-2615 (2003).

Khiar N., Fernandez I., Alcudia F. Asymmetric synthesis of optically pure tert-butyl sulfoxides using the DAG methodology, Tetrahedron Lett., 35, 5719-5722 (1994).

Copeland G. T., Miller S. J. Selection of enantioselective acyl transfer catalysts from a pooled peptide library through fluorescence-based activity assay: An approach to kenetic resolution of secondary alcohol of broad structural scope, J. Am. Chem. Soc., 123, 6496-6502 (2001).

H. R. Moon, W. J. Choi, H. O. Kim, L. S. Jeong. Improved and alternative synthesis of D- and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides, Tetrahedron: Asymmetry, 13, 1189-1193 (2002).

Christopher K. S., Vladimir P. M., Romas J. K. Subtilisin-Catalyzed Resolution of N-Acyl Aryl sulfinamides, J. Am. Chem. Soc., 127, 2104-2113 (2005).

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