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Catalytic Enantioselective Henry Reactions of Isatins: Application in the Concise Synthesis of ( S )‐(−)‐Spirobrassinin
Author(s) -
Liu Lu,
Zhang Shilei,
Xue Fei,
Lou Guangshun,
Zhang Haoyi,
Ma Shichao,
Duan Wenhu,
Wang Wei
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101025
Subject(s) - enantioselective synthesis , isatin , catalysis , chemistry , combinatorial chemistry , computer science , organic chemistry
When isatin a cat! A highly efficient, cupreine‐catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of ( S )‐(−)‐spirobrassinin without the need for protecting groups.