Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Bo Zhu, Wen Zhang, Richmond Lee, Zhiqiang Han, Wenguo Yang, Davin Tan, Kuo-Wei Huang, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

135 Scopus citations

Abstract

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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish (US)
Pages (from-to)6666-6670
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number26
DOIs
StatePublished - May 3 2013

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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