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Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita-Baylis-Hillman Carbonates with Water
Journal article   Peer reviewed

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, Vol.76(16), pp.6894-6900
19/08/2011
DOI: https://doi.org/10.1021/jo201096e
PMID: 21751799

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
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 O-18-labeling experiments.

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