Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

Alexander S. Dudnik; Todd Schwier; Vladimir Gevorgyan

doi:10.1016/j.tet.2008.10.109

Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan

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

62 Scopus citations

Abstract

A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.

Original language	English (US)
Pages (from-to)	1859-1870
Number of pages	12
Journal	Tetrahedron
Volume	65
Issue number	9
DOIs	https://doi.org/10.1016/j.tet.2008.10.109
State	Published - Feb 28 2009
Externally published	Yes

Keywords

1,3-Dienes
Gold
Naphthalenes
Propargylic esters

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.10.109

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title = "Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes",

abstract = "A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.",

keywords = "1,3-Dienes, Gold, Naphthalenes, Propargylic esters",

author = "Dudnik, {Alexander S.} and Todd Schwier and Vladimir Gevorgyan",

note = "Funding Information: The support of the National Institutes of Health (Grant GM-64444) is gratefully acknowledged. ",

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T1 - Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

AU - Dudnik, Alexander S.

AU - Schwier, Todd

AU - Gevorgyan, Vladimir

N1 - Funding Information: The support of the National Institutes of Health (Grant GM-64444) is gratefully acknowledged.

PY - 2009/2/28

Y1 - 2009/2/28

N2 - A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.

AB - A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.

KW - 1,3-Dienes

KW - Gold

KW - Naphthalenes

KW - Propargylic esters

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DO - 10.1016/j.tet.2008.10.109

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Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

Abstract

Keywords

ASJC Scopus subject areas

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