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One‐Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro‐Stereocenters
Author(s) -
Liu YunLin,
Wang Xin,
Zhao YuLei,
Zhu Feng,
Zeng XingPing,
Chen Long,
Wang CuiHong,
Zhao XiaoLi,
Zhou Jian
Publication year - 2013
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.201307250
Subject(s) - stereocenter , annulation , isatin , moiety , stereoselectivity , tandem , chemistry , stereochemistry , sequence (biology) , halogenation , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , biochemistry , materials science , composite material
All in a sequence : An organocatalyzed Morita–Baylis–Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro‐stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin‐derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.