A new chiral phosphine oxide ligand for enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides

A new set of phosphorus-containing chiral ligands has been synthesized and used with silver(I) for the catalytic asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides. One of these ligands ( POFAM6) was found to produce an effective catalyst for the asymmetric 1,3-dipolar cycloaddition...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 21; no. 20; pp. 2535 - 2541
Main Authors Eröksüz, Serap, Dogan, Özdemir, Garner, Philip P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.10.2010
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
EFFICIENT SYNTHESIS
ALKENES
CATALYSTS
ESTERS
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Summary:A new set of phosphorus-containing chiral ligands has been synthesized and used with silver(I) for the catalytic asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides. One of these ligands ( POFAM6) was found to produce an effective catalyst for the asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides with electron deficient dipolarophiles to form pyrrolidines in up to 97% yield and 89% ee.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.10.002