Projects per year
Treatment of urea or carbamate derived benzomorpholines with LDA generates N-vinylureas or N-vinylcarbamates by elimination of a phenoxide anion, cleaving the benzomorpholine ring. Simultaneous formation of a carbanion to an aryl or nitrile stabilising group allows migration of the newly-formed N-vinyl substituent to the carbanionic centre, in some cases with high enantiospecificity. Mild hydrolysis of the resulting urea or carbamate returns a C-vinylated amine, alcohol or hydantoin, in some cases with high enantiomeric purity. This ‘masked’ vinylation strategy avoids the need to use the reactive and volatile vinyl isocyanate as a starting material.
- Benzylic anions
- Tertiary stereocentre
1/07/15 → 31/05/18
Corbet, B., Matlock, J., Mas Rosello, J., & Clayden, J. (2017). Intramolecular vinylation of carbanions using N-acyl benzomorpholines as masked vinylureas and vinylcarbamates. Comptes Rendus Chimie, 20(6), 634-642. https://doi.org/10.1016/j.crci.2017.01.006