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Polaske NW, Dubey R, Nichol GS, et al. Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines. Tetrahedron Asymmetry. 2009;20(23):2742-2750doi: 10.1016/j.tetasy.2009.10.037.
Polaske, N. W., Dubey, R., Nichol, G. S., & Olenyuk, B. (2009). Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines. Tetrahedron, asymmetry, 20(23), 2742-2750. https://doi.org/10.1016/j.tetasy.2009.10.037
Polaske, Nathan W, et al. "Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines." Tetrahedron, asymmetry vol. 20,23 (2009): 2742-2750. doi: https://doi.org/10.1016/j.tetasy.2009.10.037
Polaske NW, Dubey R, Nichol GS, Olenyuk B. Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines. Tetrahedron Asymmetry. 2009 Dec 11;20(23):2742-2750. doi: 10.1016/j.tetasy.2009.10.037. PMID: 20161615; PMCID: PMC2811878.
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Tetrahedron Asymmetry. 2009 Dec 11;20(23):2742-2750. doi: 10.1016/j.tetasy.2009.10.037.

Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

Tetrahedron, asymmetry

Nathan W Polaske, Ramin Dubey, Gary S Nichol, Bogdan Olenyuk

Affiliations

  1. Department of Chemistry and Biochemistry, The University of Arizona, 1306 E University Blvd, Tucson, AZ 85721, USA.

PMID: 20161615 PMCID: PMC2811878 DOI: 10.1016/j.tetasy.2009.10.037

Abstract

The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported.

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