Facile synthesis of spirocyclic ketones via gold(I)-catalyzed claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols

Ming-Chang P. Yeh, Hui Fen Pai, Chuen Yo Hsiow, Yan Rong Wang

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The gold(I)-catalyzed Claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols proceeds via a cationic allylic vinyl ether gold intermediate to give spirocyclic ketones. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate the spirocyclic ketones. This transformation can be applied to the synthesis of aza- and oxaspirocyclic ketones from cyclic 8-aryl-2,7-enyn-l-ols bearing an N-sulfonamide or an oxygen atom linkage in the tether and the gold(I) catalyst.

Original languageEnglish
Pages (from-to)160-166
Number of pages7
JournalOrganometallics
Volume29
Issue number1
DOIs
Publication statusPublished - 2010 Jan 11

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Facile synthesis of spirocyclic ketones via gold(I)-catalyzed claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols'. Together they form a unique fingerprint.

  • Cite this