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Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

ABSTRACT: 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.

SUBMITTER: Dudnik AS 

PROVIDER: S-EPMC3679922 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

Dudnik Alexander S AS   Schwier Todd T   Gevorgyan Vladimir V  

Organic letters 20080301 7

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. ...[more]

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