doi: 10.1021/jo201096e.
Epub 2011 Jul 22.
Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
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- PMID: 21751799
- DOI: 10.1021/jo201096e
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Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
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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