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