Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water.

Abstract

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 (18)O-labeling experiments.

DOI: 10.1021/jo201096e

Cite this paper

@article{Zhu2011LewisBC, title={Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water.}, author={Bo Zhu and Lin Yan and Yuanhang Pan and Richmond Lee and HongJun Liu and Zhiqiang Han and Kuo-wei Huang and Choon-Hong Tan and Zhiyong Jiang}, journal={The Journal of organic chemistry}, year={2011}, volume={76 16}, pages={6894-900} }