☆ 4.7 Article

Donor-Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4+2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton

JOURNAL OF ORGANIC CHEMISTRY (2015)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 80, 期 16, 页码 8225-8235

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.5b01179

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Chemistry, Organic

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Russian Science Foundation [14-13-01054]
Russian Science Foundation [14-13-01054] Funding Source: Russian Science Foundation

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摘要

A new process for (4 + 2)-annulation of donor-acceptor cyclopropanes (DACs) with unsaturated compounds in the presence of anhydrous GaCl3 has been developed. In this process, DACs act as sources of formal 1,2- and 1,4-dipoles to give polysubstituted tetralins in high yields and with high regio- and diastereoselectivity. Alkenes with both aryl and alkyl substituents at the double bond undergo this reaction equally readily. A most likely mechanism of the reaction has been proposed. It involves preliminary generation of a key 1,2-dipolar gallium complex and its subsequent participation in annulation with an alkene.

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