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Chemistry. 2015 Jan 7;21(2):559-64. doi: 10.1002/chem.201405190. Epub 2014 Nov 19.

Gold(I)-catalyzed 1,4- and/or 1,5-heteroaryl migration reactions through regiocontrolled cyclizations.

Author information

1
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P. R. China); Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 (P. R. China).

Abstract

Gold(I)-catalyzed regioselective cycloisomerizations of furan-ynes have been described. The reaction provides a concise access to stereodefined trisubstituted alkenes by endo cyclization with concomitant 1,5-migration of the furanyl group in the presence of unactivated 3 Å molecular sieves. In the absence of molecular sieves, indene products are generated by exo cyclization, followed by 1,4-furanyl migration/cyclization. The scope for 1,5-migrations can be extended to other heterocycles, such as benzofurans, thiophenes, and pyrroles.

KEYWORDS:

alkenes; furans; gold catalysis; migration; stereoselectivity

PMID:
25411108
DOI:
10.1002/chem.201405190
[Indexed for MEDLINE]

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