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Asymmetric Nitroaldol Reactions of Nitroalkanes with Isatins Catalyzed by Bifunctional Cinchona Alkaloid Derivatives
Author(s) -
Li MeiQiu,
Zhang JinXin,
Huang XiaoFei,
Wu Bin,
Liu ZhaoMin,
Chen Jian,
Li XiangDong,
Wang XingWang
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100824
Subject(s) - cinchona , chemistry , bifunctional , nitroaldol reaction , nitromethane , organocatalysis , enantioselective synthesis , cinchona alkaloids , organic chemistry , oxindole , catalysis , indolizidine , alkaloid , isatin , michael reaction
The enantioselective nitroaldol reactions of isatins with nitroalkanes were smoothly carried out by organocatalysis. A C6′‐OH cinchona alkaloid derivative bearing a C9‐OBn group exhibited outstanding catalytic efficiency as an acid–base bifunctional catalyst for the nitroaldol reaction of isatins with nitromethane, providing 3‐hydroxy‐3‐(nitromethyl)indolin‐2‐ones in good yields (90–98 %) and with good to high enantiomeric excess values (72–95 %). The resultant oxindole derivatives are highly important for the synthesis of related natural products and pharmaceutically active compounds.