Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

Handle URI:
http://hdl.handle.net/10754/561777
Title:
Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis
Authors:
Liu, Chen; Zhu, Qiang; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Lu, Yixin
Abstract:
A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 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:
Organic Letters
Issue Date:
20-May-2011
DOI:
10.1021/ol200747x
PubMed ID:
21510614
Type:
Article
ISSN:
15237060
Sponsors:
We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112).
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.authorLiu, Chenen
dc.contributor.authorZhu, Qiangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorLu, Yixinen
dc.date.accessioned2015-08-03T09:04:22Zen
dc.date.available2015-08-03T09:04:22Zen
dc.date.issued2011-05-20en
dc.identifier.issn15237060en
dc.identifier.pmid21510614en
dc.identifier.doi10.1021/ol200747xen
dc.identifier.urihttp://hdl.handle.net/10754/561777en
dc.description.abstractA novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.en
dc.description.sponsorshipWe are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112).en
dc.publisherAmerican Chemical Societyen
dc.titlePrimary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysisen
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.journalOrganic Lettersen
dc.contributor.institutionDepartment of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
kaust.authorHuang, Kuo-Weien
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.