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Issue 60, 2018
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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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Article information


Submitted
09 May 2018
Accepted
03 Jul 2018
First published
03 Jul 2018

Chem. Commun., 2018,54, 8343-8346
Article type
Communication

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, 54, 8343
DOI: 10.1039/C8CC03760D

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