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Asymmetric Construction of Spirooxindoles by Organocatalytic Multicomponent Reactions Using Diazooxindoles
Author(s) -
Wu MingYue,
He WeiWei,
Liu XinYuan,
Tan Bin
Publication year - 2015
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.201504640
Subject(s) - stereocenter , nitroalkene , enantioselective synthesis , chemistry , catalysis , organocatalysis , functional group , combinatorial chemistry , hydrogen bond , organic chemistry , molecule , polymer
The first highly diastereo‐ and enantioselective multicomponent reaction of diazooxindoles, nitrosoarenes, and nitroalkenes using a newly developed hydrogen‐bond catalyst has been successfully developed for the efficient construction of a series of spirooxindole derivatives with excellent functional‐group tolerance. Spirooxindoles are formed in excellent yields and stereoselectivities, and the method represents an unprecedented approach for trapping the active intermediate with a nitroalkene to form biologically important compounds having three contiguous stereogenic centers with excellent asymmetric induction.