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

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 al...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 54; no. 60; pp. 8343 - 8346
Main Authors Guisan-Ceinos, Manuel, Martin-Heras, Victor, Soler-Yanes, Rita, Cardenas, Diego J., Tortosa, Mariola
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Allene
Chemistry
Chemistry, Multidisciplinary
Cross coupling
Physical Sciences
Racemization
Reagents
Science & Technology
ALCOHOLS
CHIRAL ALLENES
ETHERS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
BONDS
PHOSPHATES
ACETATES
SYN
ARYL
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Summary: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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ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc03760d