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Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles
Author(s) -
Hanhan Nadine V.,
BallJones Nicolas R.,
Tran Ngon T.,
Franz Annaliese K.
Publication year - 2012
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.201105739
Subject(s) - annulation , catalysis , trimethylsilyl , chemistry , combinatorial chemistry , reaction conditions , silylation , organic chemistry , medicinal chemistry
Silyl‐inspired spirocycle : The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2 (SbF 6 )/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The SiC bond can be oxidized to deliver hydroxy‐substituted spirooxindoles. TMS=trimethylsilyl.
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