Download PDF
Synfacts 2010(8): 0948-0948  
DOI: 10.1055/s-0030-1257803
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric [3+2] Cycloaddition Catalyzed by 1,2-Aminophosphanes

Contributor(s): Benjamin List, Ji-Woong Lee
H. Xiao, Z. Chai, C.-W. Zheng, Y.-Q. Yang, W. Liu, J.-K. Zhang, G. Zhao*
University of Science and Technology of China, Hefei and Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
22 July 2010 (online)

    Permissions and Reprints

Significance

The authors report highly regio- and enantioselective [3+2] cycloadditions of arylidenemalononitrile and its derivatives 2 with ­allenoate 3 catalyzed by α-amino acid derived 1,2-aminophosphanes, such as 1, as bifunctional catalysts. The optimal catalyst 1 proved efficient for a broad substrate scope for the electron-­deficient olefins 2, derived from various aromatic aldehydes, in terms of chemical yield and stereoselectivity. The obtained enantioenriched products 4 can be transformed into highly functionalized ­cyclopentanes 6 in good to excellent yield with high diastereoselectivity.