A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.
Bibliographical noteKAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.
ASJC Scopus subject areas
- Organic Chemistry