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Synfacts 2011(2): 0214-0214  
DOI: 10.1055/s-0030-1259356
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Entry to Chiral Pyrroloindolines

Contributor(s): Benjamin List, Olga Lifchits
X. Li, S. Luo*, J.-P. Cheng
Institute of Chemistry, Chinese Academy of Sciences, Beijing and Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

Luo and co-workers report an asymmetric conjugate addition of oxindoles 1 to 2-chloroacrylonitrile (2) using their previously developed bifunctional thiourea catalyst 4. The generated products 3, featuring two non-contiguous stereocenters, were formed with an impressive level of diastereo- and enantiocontrol and a wide scope. The method was shown to work well on preparative scale, and the utility of the products was demonstrated by elaborating 3 to various skeletons of indole alkaloids (e.g. 6).