Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
Type
ArticleAuthors
Zhu, BoYan, Lin
Pan, Yuanhang
Lee, Richmond
Liu, Hongjun
Han, Zhiqiang
Huang, Kuo-Wei

Tan, Choonhong
Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2011-08-19Permanent link to this record
http://hdl.handle.net/10754/561844
Metadata
Show full item recordAbstract
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.Citation
Zhu, B., Yan, L., Pan, Y., Lee, R., Liu, H., Han, Z., … Jiang, Z. (2011). Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water. The Journal of Organic Chemistry, 76(16), 6894–6900. doi:10.1021/jo201096eSponsors
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 ChemistryPubMed ID
21751799ae974a485f413a2113503eed53cd6c53
10.1021/jo201096e
Scopus Count
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