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Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes

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Abstract

Herein we describe a robust and practical method to prepare enantiomerically enriched trisubstituted allenes using alkyl Grignard reagents and bench stable propargylic ammonium salts. Excellent yields as well as regio- and stereoselectivities are observed. Our conditions provide a solution to the allene racemization, which has been a long-standing problem when using Grignard reagents.

Graphical abstract: Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes

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Publication details

The article was received on 09 May 2018, accepted on 03 Jul 2018 and first published on 03 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC03760D
Citation: Chem. Commun., 2018, Advance Article
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    Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes

    M. Guisán-Ceinos, V. Martín-Heras, R. Soler-Yanes, D. J. Cárdenas and M. Tortosa, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC03760D

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