Gold-catalyzed double migration-benzannulation cascade toward naphthalenes

Alexander S. Dudnik; Todd Schwier; Vladimir Gevorgyan

doi:10.1021/ol800229h

Gold-catalyzed double migration-benzannulation cascade toward naphthalenes

Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan

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

93 Scopus citations

Abstract

(Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.

Original language	English (US)
Pages (from-to)	1465-1468
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	7
DOIs	https://doi.org/10.1021/ol800229h
State	Published - Apr 3 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol800229h

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abstract = "(Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.",

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doi = "10.1021/ol800229h",

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AU - Dudnik, Alexander S.

AU - Schwier, Todd

AU - Gevorgyan, Vladimir

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N2 - (Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.

AB - (Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.

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Gold-catalyzed double migration-benzannulation cascade toward naphthalenes

Abstract

ASJC Scopus subject areas

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