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. 2011 Aug 19;76(16):6894-900.
doi: 10.1021/jo201096e. Epub 2011 Jul 22.

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

Bo Zhu  1 , Lin Yan, Yuanhang Pan, Richmond Lee, Hongjun Liu, Zhiqiang Han, Kuo-Wei Huang, Choon-Hong Tan, Zhiyong Jiang
Affiliations

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

Bo Zhu et al. J Org Chem. .

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.

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