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-VCH Verlag
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.
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-VCH Verlagen
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
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