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Org Lett. 2013 Aug 2;15(15):3978-81. doi: 10.1021/ol401881n. Epub 2013 Jul 19.

Organocatalyzed anion relay leading to functionalized 2,3-dihydrofurans.

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  • 1Department of Chemistry, Northeast Normal University, Changchun 130024, China.

Abstract

A DABCO-mediated organocatalyzed anion relay cascade based on 1-cinnamoylcyclopropanecarboxamides has been developed and applied in the construction of 2,3-dihydrofurans with the original alkene and amide functionalities intact. In the aza-oxy-carbanion relay process, DABCO provides both the electron source and sink. The enolate anion-triggered ring opening of the cyclopropane is ascribed to the key step in the anion relay cascade.

PMID:
23869601
[PubMed - indexed for MEDLINE]
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