Combined InCl₃- and Amine-Catalyzed Intramolecular Addition of α-Disubstituted Aldehydes onto Unactivated Alkynes

Benjamin Montaignac, Maxime R. Vitale, Veronique Michelet* and Virginie Ratovelomanana-Vidal*

*ENSCP, Chimie ParisTech, UMR 7223, Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75231 Paris Cedex 05, France, Email: veronique-micheletchimie-paristech.fr, virginie-vidalchimie-paristech.fr

B. Montaignac, M. R. Vitale, V. Michelet, V. Ratovelomanana-Vidal, Org. Lett., 2010, 12, 2582-2585.

DOI: 10.1021/ol100729t

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Abstract

InCl₃ and (Cy)(i-Pr)NH efficiently promote the carbocyclization reaction of α-disubstituted aldehydes to give functionalized cyclopentanes in very good yields through a combination of enamine-type catalysis with an indium-catalyzed activation of alkynes.

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Key Words

Cyclopentanes

ID: J54-Y2010-1590

Combined InCl3- and Amine-Catalyzed Intramolecular Addition of α-Disubstituted Aldehydes onto Unactivated Alkynes

Benjamin Montaignac, Maxime R. Vitale, Veronique Michelet* and Virginie Ratovelomanana-Vidal*

Combined InCl₃- and Amine-Catalyzed Intramolecular Addition of α-Disubstituted Aldehydes onto Unactivated Alkynes