Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: Stereospecific synthesis of allenes
Entity
UAM. Departamento de Química Orgánica; UAM. Instituto de Investigación Avanzada en Ciencias Químicas (IAdChem)Publisher
The Royal Society of ChemistryDate
2018-03-21Citation
10.1039/c8cc03760d
Chemical Communications 54.60 (2018): 8343-8346
ISSN
1359-7345 (print); 1364-548X (online)DOI
10.1039/c8cc03760dEditor's Version
http://doi.org/10.1039/c8cc03760dSubjects
Grignard reagents; Ammonium salts; Racemization; Allenes; Copper-catalysed; QuímicaRights
© 2018 The Royal Society of ChemistryAbstract
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.
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Google Scholar:Guisán-Ceinos, Manuel
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Martín-Heras, Víctor
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Soler-Yanes, Rita
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Cárdenas Morales, Diego Jesús
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Tortosa Manzanares, Mariola
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