Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 13, Pages 3387-3391Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309982
Keywords
boron; conjugate additions; enantioselective synthesis; N-heterocyclic carbenes; organic synthesis
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Funding
- NIH [GM-57212]
- NSF [CHE-1111074]
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The first examples of Lewis base catalyzed enantioselective boryl conjugate additions (BCAs) that generate products containing boron-substituted quaternary carbon stereogenic centers are disclosed. Reactions are performed in the presence of 1.0-5.0mol% of a readily accessible chiral accessible N-heterocyclic carbene (NHC) and commercially available bis(pinacolato)diboron; cyclic or linear ,-unsaturated ketones can be used and rigorous exclusion of air or moisture is not necessary. The desired products are obtained in 63-95% yield and 91:9 to >99:1 enantiomeric ratio (e.r.). The special utility of the NHC-catalyzed approach is demonstrated in the context of an enantioselective synthesis of natural product antifungal (-)-crassinervic acid.
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