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Asymmetric Synthesis of Fully Substituted Cyclopentane‐Oxindoles through an Organocatalytic Triple Michael Domino Reaction
Author(s) -
Zou LiangHua,
Philipps Arne R.,
Raabe Gerhard,
Enders Dieter
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406047
Subject(s) - stereocenter , domino , michael reaction , cyclopentanes , moiety , organocatalysis , cyclopentane , cascade reaction , chemistry , oxindole , stereoselectivity , enantioselective synthesis , triple bond , combinatorial chemistry , wittig reaction , stereochemistry , organic chemistry , catalysis , double bond
An efficient, highly stereoselective asymmetric synthesis of fully functionalized cyclopentanes bearing an oxindole moiety and several other functional groups in one pot has been developed. Key step is an organocatalytic triple Michael domino reaction forming three CC bonds and six stereocenters, including a quaternary one. Starting from equimolar amounts of simple substrates, a high molecular complexity can be reached after a Wittig olefination in one pot. The new protocol can easily be scaled up to gram amounts.