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

Access to Document

10.1021/om900833k

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

@article{54e5b42c742240ba8da62a2838f6e512,

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

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.",

author = "Yeh, {Ming-Chang P.} and Pai, {Hui Fen} and Hsiow, {Chuen Yo} and Wang, {Yan Rong}",

year = "2010",

month = jan,

day = "11",

doi = "10.1021/om900833k",

language = "English",

volume = "29",

pages = "160--166",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Facile synthesis of spirocyclic ketones via gold(I)-catalyzed claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols

AU - Yeh, Ming-Chang P.

AU - Pai, Hui Fen

AU - Hsiow, Chuen Yo

AU - Wang, Yan Rong

PY - 2010/1/11

Y1 - 2010/1/11

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=73649094076&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=73649094076&partnerID=8YFLogxK

U2 - 10.1021/om900833k

DO - 10.1021/om900833k

M3 - Article

AN - SCOPUS:73649094076

VL - 29

SP - 160

EP - 166

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 1

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this