Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 4, Pages 1466-1475Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202318
Keywords
allylic compounds; asymmetric synthesis; Grignard reagents; heterocyclic carbenes; quaternary stereocentres
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Funding
- Swiss National Research Foundation [200020-126663]
- COST action D40 (SER) [C07.0097]
- Swiss National Science Foundation (SNF) [200020_126663] Funding Source: Swiss National Science Foundation (SNF)
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The Cu-free asymmetric allylic alkylation, catalysed by NHC, with Grignard reagents is reported on allyl bromide derivatives with good results. The enantioselectivity was quite homogeneous (around 85?% ee) on large and various substrates, regardless of the nature of the Grignard reagent. The formation of stereogenic quaternary centres was highly regioselective for both aliphatic and aromatic derivatives with good enantiomeric excess (up to 92?% ee). The methodology developed was found to be complementary with the Cu-catalysed version. Several new NHCs were tested with improved efficiency. In addition, mechanistic studies, using NMR spectroscopy, led to the discovery of the catalytically active species.
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