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Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
Authors:Zhu Bo  Yan Lin  Pan Yuanhang  Lee Richmond  Liu Hongjun  Han Zhiqiang  Huang Kuo-Wei  Tan Choon-Hong  Jiang Zhiyong
Institution:Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, People's Republic of China.
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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