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- Title
Enantioselective Synthesis of Boron-Substituted Quaternary Carbon Stereogenic Centers through NHC-Catalyzed Conjugate Additions of (Pinacolato)boron Units to Enones.
- Authors
Radomkit, Suttipol; Hoveyda, Amir H.
- Abstract
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 1.0-5.0 mol % of a readily accessible chiral accessible N-heterocyclic carbene (NHC) and commercially available bis(pinacolato)diboron; cyclic or linear α,β-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.
- Subjects
ENANTIOSELECTIVE catalysis; BORON; CARBON; CHEMICAL reactions; HETEROCYCLIC compounds; CARBENE analogues; KETONES
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 13, p3387
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201309982