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Synfacts 2011(8): 0908-0908  
DOI: 10.1055/s-0030-1260844
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Henry Reaction of Isatins

Contributor(s): Benjamin List, Olga Lifchits
L. Liu, S. Zhang, F. Xue, G. Lou, H. Zhang, S. Ma, W. Duan, W. Wang*
East China University of Science and Technology, Shanghai, P. R. of China and University of New Mexico, Albuquerque, USA
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

Wang, Duan and colleagues report a catalytic enantioselective Henry reaction between isatins 1 and nitroalkanes 2 using the simple cinchona alkaloid cupreine (3). The resulting hydroxyoxindole derivatives 4 were isolated with excellent yields and, for the first time, with good to high enantioselectivities. This column-chromatography-free methodology was applied as key step in a concise total synthesis of natural products (+)-dioxibrassinin (5) and (S)-(-)-spirobrassinin (6).