Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

Handle URI:
http://hdl.handle.net/10754/561730
Title:
Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions
Authors:
Ma, Ting; Fu, Xiao; Kee, Choonwee; Zong, Lili; Pan, Yuanhang; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Choonhong
Abstract:
A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 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 (ACS)
Journal:
Journal of the American Chemical Society
Issue Date:
9-Mar-2011
DOI:
10.1021/ja1098353
Type:
Article
ISSN:
00027863
Sponsors:
This work was supported by a research grant (R-143-000-342-112) and a scholarship (to M.T.) from NUS.
Is Supplemented By:
Ma, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836212: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24lp; DOI:10.5517/ccx24lp; HANDLE:http://hdl.handle.net/10754/624654; Ma, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836213: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24mq; DOI:10.5517/ccx24mq; HANDLE:http://hdl.handle.net/10754/624655
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.authorMa, Tingen
dc.contributor.authorFu, Xiaoen
dc.contributor.authorKee, Choonweeen
dc.contributor.authorZong, Lilien
dc.contributor.authorPan, Yuanhangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Choonhongen
dc.date.accessioned2015-08-03T09:03:18Zen
dc.date.available2015-08-03T09:03:18Zen
dc.date.issued2011-03-09en
dc.identifier.issn00027863en
dc.identifier.doi10.1021/ja1098353en
dc.identifier.urihttp://hdl.handle.net/10754/561730en
dc.description.abstractA new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.en
dc.description.sponsorshipThis work was supported by a research grant (R-143-000-342-112) and a scholarship (to M.T.) from NUS.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titlePentanidium-catalyzed enantioselective phase-transfer conjugate addition reactionsen
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 the American Chemical Societyen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByMa, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836212: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24lpen
dc.relation.isSupplementedByDOI:10.5517/ccx24lpen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624654en
dc.relation.isSupplementedByMa, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836213: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24mqen
dc.relation.isSupplementedByDOI:10.5517/ccx24mqen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624655en
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