Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement

Hongmiao Wu, Weiwei Zi, Guigen Li, Hongjian Lu, F. Dean Toste

Research output: Contribution to journalArticle

35 Scopus citations

Abstract

An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.

Original languageEnglish
Pages (from-to)8529-8532
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number29
DOIs
StatePublished - Jul 13 2015

Keywords

  • Claisen rearrangement
  • alkoxylation
  • desymmetrization
  • enantioselectivity
  • gold

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