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Synfacts 2011(11): 1240-1240  
DOI: 10.1055/s-0031-1289262
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Spirooxindoles

Contributor(s): Benjamin List, Nathalie Dupré
Y. Cao, X. Jiang, L. Liu, F. Shen, F. Zhang, R. Wang*
Lanzhou University and The Hong Kong University, P. R. of China
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

Wang and co-workers report the enantioselective synthesis of densely functionalized 3,3′-thiopyrrolidonyl spirooxindoles having three contiguous stereogenic centers. This reaction combines α-isothiocyanatoimides, methyl­eneindolinone derivatives and a rosin-derived tertiary amine thiourea as catalyst and proceeds through a Michael-cyclization sequence. The products are obtained with good yield, diastereo­selectivity, and enantioselectivity.