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

Handle URI:
http://hdl.handle.net/10754/561844
Title:
Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water
Authors:
Zhu, Bo; Yan, Lin; Pan, Yuanhang; Lee, Richmond; Liu, Hongjun; Han, Zhiqiang; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Choonhong; Jiang, Zhiyong
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry
Issue Date:
19-Aug-2011
DOI:
10.1021/jo201096e
PubMed ID:
21751799
Type:
Article
ISSN:
00223263
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.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorZhu, Boen
dc.contributor.authorYan, Linen
dc.contributor.authorPan, Yuanhangen
dc.contributor.authorLee, Richmonden
dc.contributor.authorLiu, Hongjunen
dc.contributor.authorHan, Zhiqiangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Choonhongen
dc.contributor.authorJiang, Zhiyongen
dc.date.accessioned2015-08-03T09:32:17Zen
dc.date.available2015-08-03T09:32:17Zen
dc.date.issued2011-08-19en
dc.identifier.issn00223263en
dc.identifier.pmid21751799en
dc.identifier.doi10.1021/jo201096een
dc.identifier.urihttp://hdl.handle.net/10754/561844en
dc.description.abstractA 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.en
dc.description.sponsorshipFinancial 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.en
dc.publisherAmerican Chemical Societyen
dc.titleLewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with wateren
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalJournal of Organic Chemistryen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, Chinaen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien

Related articles on PubMed

All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.