title: Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water.
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.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, People's Republic of China.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhu
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Yuanhang
authors.initials: Y
authors.lastname: Pan
authors.forename: Richmond
authors.initials: R
authors.lastname: Lee
authors.forename: Hongjun
authors.initials: H
authors.lastname: Liu
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Han
authors.forename: Kuo-Wei
authors.initials: KW
authors.lastname: Huang
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D058115:Lewis Bases / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000438:Alcohols; D002254:Carbonates; D058115:Lewis Bases; D014867:Water