The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

Handle URI:
http://hdl.handle.net/10754/561702
Title:
The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives
Authors:
Luo, Jie; Wang, Haifei; Han, Xiao; Xu, Liwen; Kwiatkowski, Jacek; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Lu, Yixin
Abstract:
Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
11-Jan-2011
DOI:
10.1002/anie.201006316
PubMed ID:
21328657
Type:
Article
ISSN:
14337851
Sponsors:
We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.
Is Supplemented By:
Luo, J., Wang, H., Han, X., Xu, L.-W., Kwiatkowski, J., Huang, K.-W., & Lu, Y. (2011). CCDC 803555: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvz543; DOI:10.5517/ccvz543; HANDLE:http://hdl.handle.net/10754/624624
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.authorLuo, Jieen
dc.contributor.authorWang, Haifeien
dc.contributor.authorHan, Xiaoen
dc.contributor.authorXu, Liwenen
dc.contributor.authorKwiatkowski, Jaceken
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorLu, Yixinen
dc.date.accessioned2015-08-03T09:02:40Zen
dc.date.available2015-08-03T09:02:40Zen
dc.date.issued2011-01-11en
dc.identifier.issn14337851en
dc.identifier.pmid21328657en
dc.identifier.doi10.1002/anie.201006316en
dc.identifier.urihttp://hdl.handle.net/10754/561702en
dc.description.abstractTwice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en
dc.description.sponsorshipWe thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.en
dc.publisherWiley-Blackwellen
dc.subjectaldol reactionen
dc.subjectasymmetric synthesisen
dc.subjectbutenolidesen
dc.subjectglycerol derivativesen
dc.subjectorganocatalysisen
dc.titleThe direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivativesen
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.journalAngewandte Chemie International Editionen
dc.contributor.institutionDepartment of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
dc.contributor.institutionKey Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Chinaen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByLuo, J., Wang, H., Han, X., Xu, L.-W., Kwiatkowski, J., Huang, K.-W., & Lu, Y. (2011). CCDC 803555: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvz543en
dc.relation.isSupplementedByDOI:10.5517/ccvz543en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624624en
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