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Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters
Author(s) -
Bencivenni Giorgio,
Wu LiYuan,
Mazzanti Andrea,
Giannichi Berardino,
Pesciaioli Fabio,
Song MaoPing,
Bartoli Giuseppe,
Melchiorre Paolo
Publication year - 2009
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.200903192
Subject(s) - stereocenter , catalysis , combinatorial chemistry , chemistry , trimethylsilyl , stereochemistry , enantioselective synthesis , computer science , organic chemistry
Not so complex : The asymmetric one‐step construction of multiple stereocenters in complex spirocyclic oxindoles was achieved with very high fidelity by using distinct organocascade reactions utilizing two organocatalysts, each activating different carbonyl compounds (see scheme; TMS=trimethylsilyl). The complementary approaches demonstrate the potential of organocascade catalysis to face challenging synthetic problems.