Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

Type
Article
Authors
Zhu, Bo
Yan, Lin
Pan, Yuanhang
Lee, Richmond
Liu, Hongjun
Han, Zhiqiang
Huang, Kuo-Wei cc
Tan, Choonhong
Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
HCL
Date
2011-08-19

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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 18O-labeling experiments. © 2011 American Chemical Society.
Sponsors
Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.
Publisher
American Chemical Society (ACS)
Journal
The Journal of Organic Chemistry
ISSN
00223263
DOI
10.1021/jo201096e
PubMed ID
21751799
Handle URI
http://hdl.handle.net/10754/561844
Collections
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division