Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes

Ming Chang P. Yeh; Ming Nan Lin; Yi Shiang Chou; Tern Chi Lin; Li Yu Tseng

doi:10.1021/jo200445p

Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes

Ming Chang P. Yeh, Ming Nan Lin, Yi Shiang Chou, Tern Chi Lin, Li Yu Tseng

Department of Chemistry

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

8 Citations (Scopus)

Abstract

The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.

Original language	English
Pages (from-to)	4027-4033
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	76
Issue number	10
DOIs	https://doi.org/10.1021/jo200445p
Publication status	Published - 2011 May 20

ASJC Scopus subject areas

Organic Chemistry

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Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes. / Yeh, Ming Chang P.; Lin, Ming Nan; Chou, Yi Shiang; Lin, Tern Chi; Tseng, Li Yu.

In: Journal of Organic Chemistry, Vol. 76, No. 10, 20.05.2011, p. 4027-4033.

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

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abstract = "The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.",

author = "Yeh, {Ming Chang P.} and Lin, {Ming Nan} and Chou, {Yi Shiang} and Lin, {Tern Chi} and Tseng, {Li Yu}",

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AU - Yeh, Ming Chang P.

AU - Lin, Ming Nan

AU - Chou, Yi Shiang

AU - Lin, Tern Chi

AU - Tseng, Li Yu

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AB - The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.

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Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes

Abstract

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