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

doi:10.1021/om900833k

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	160-166
Number of pages	7
Journal	Organometallics
Volume	29
Issue number	1
DOIs	https://doi.org/10.1021/om900833k
Publication status	Published - 2010 Jan 11

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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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.",

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AU - Hsiow, Chuen Yo

AU - Wang, Yan Rong

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AB - 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.

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

Abstract

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