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Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3‐Hydroxyamino‐2‐Oxindoles Using Nitrosoarenes
Author(s) -
Shen Ke,
Liu Xiaohua,
Wang Gang,
Lin Lili,
Feng Xiaoming
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100758
Subject(s) - enantioselective synthesis , scope (computer science) , combinatorial chemistry , substrate (aquarium) , catalysis , transformation (genetics) , action (physics) , scale (ratio) , computer science , chemistry , organic chemistry , programming language , geography , physics , biology , cartography , ecology , biochemistry , quantum mechanics , gene
Sc takes action : The highly enantioselective hydroxyamination reaction of N‐unprotected 2‐oxindoles with nitrosoarenes has been realized using the Sc(OTf) 3 / L1 complex. The catalyst system exhibited remarkably broad substrate scope and high efficiency. This transformation is the first example of a chiral Sc III /enolate activating a nitrosoarene, and can be conducted on a gram scale without loss in the ee values.