Download PDF
Synfacts 2009(3): 0326-0326  
DOI: 10.1055/s-0028-1087722
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Sulfamides as Bifunctional Catalysts in Conjugate Addition Reactions

Contributor(s): Benjamin List, Steffen Müller
X.-j. Zhang, S.-p. Liu, X.-m. Li, M. Yan*, A. S. C. Chan
Sun Yat-sen University, Guangzhou, P. R. of China
Further Information

Publication History

Publication Date:
19 February 2009 (online)

    Permissions and Reprints

Significance

The authors report the synthesis of chiral sulfamides and their use as bifunctional catalysts in the conjugate addition of aldehydes to ­nitroolefines. The sulfamide primary amine catalyst 1 turned out to give the best results regarding enantioselectivity and yield. The use of Brønsted-basic additives had a beneficial effect on the reaction rate, presumably accelerating steps II and III of the catalytic cycle. The desired products were obtained in good yields and excellent enantio­selectivities.