4.8 Article

Gold-catalyzed double migration-benzannulation cascade toward naphthalenes

Journal

ORGANIC LETTERS
Volume 10, Issue 7, Pages 1465-1468

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol800229h

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Funding

  1. NIGMS NIH HHS [R01 GM064444, GM-64444] Funding Source: Medline

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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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