InCl3/CyNH2 cocatalyzed carbocyclization reaction: An entry to α-disubstituted exo -methylene cyclopentanes

DOI: 10.1021/jo1018552

Source and publish data:

Journal of Organic Chemistry p. 8322 - 8325 (2010)

Update date:2022-08-05

Topics:

Authors:

Montaignac, Benjamin

Vitale, Maxime R.

Ratovelomanana-Vidal, Virginie

Michelet, Veronique

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Article abstract of DOI:10.1021/jo1018552

An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from α-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.

Full text of DOI:10.1021/jo1018552

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