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Lewis Base Catalyzed Enantioselective Allylic Hydroxylation

of Morita-Baylis-Hillman carbonates with water


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

Journal of Organic Chemistry, 2011, 76, 6894–6900


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 18O-labeling experiments.


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