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Direct Asymmetric Vinylogous Aldol Reaction of Allyl Ketones with Isatins: Divergent Synthesis of 3‐Hydroxy‐2‐Oxindole Derivatives
Author(s) -
Zhu Bo,
Zhang Wen,
Lee Richmond,
Han Zhiqiang,
Yang Wenguo,
Tan Davin,
Huang KuoWei,
Jiang Zhiyong
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.201302274
Subject(s) - aldol reaction , oxindole , bifunctional , enantioselective synthesis , stereoselectivity , chemistry , computer science , combinatorial chemistry , catalysis , stereochemistry , organic chemistry
6 in 1 : The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E ‐configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3‐hydroxy‐2‐oxindole derivatives (e.g., CPC‐1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π–π* and H‐bonding interactions in the transition state.