Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Wen Zhang, Davin Tan, Richmond Lee, Guanghu Tong, Wenchao Chen, Baojian Qi, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

112 Scopus citations

Abstract

The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish (US)
Pages (from-to)10069-10073
Number of pages5
JournalAngewandte Chemie International Edition
Volume51
Issue number40
DOIs
StatePublished - Sep 5 2012

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Fingerprint Dive into the research topics of 'Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions'. Together they form a unique fingerprint.

Cite this