Highly selective intermolecular one-pot three component 1,3-dipolar cycloaddition reaction of aldehydes, with phosphonates and proline

The use of l-proline to act as an organocatalyst in the aldol reaction of acylphosphonates and non enolizable aldehydes failed; however, it reacted with the aldehydes to afford azomethine ylides after decarboxylation that in turn underwent 1,3-dipolar cycloaddition with the acylphosphonates to form...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 30; pp. 4329 - 4334
Main Authors Subasi, N. Tuna, Yalcinkaya, Hatice, Demir, Ayhan S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.07.2017
Elsevier
Subjects
Acylphosphonate
Azomethine ylide
Chemistry
Chemistry, Organic
Dipolar cycloaddition
Physical Sciences
Proline
Science & Technology
Proline
Acylphosphonate
Dipolar cycloaddition
Azomethine ylide
ACYL ANION EQUIVALENTS
ASYMMETRIC ALDOL REACTIONS
ACYLPHOSPHONATES
AZOMETHINE YLIDES
ORGANOCATALYSIS
GENERATION
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Summary:The use of l-proline to act as an organocatalyst in the aldol reaction of acylphosphonates and non enolizable aldehydes failed; however, it reacted with the aldehydes to afford azomethine ylides after decarboxylation that in turn underwent 1,3-dipolar cycloaddition with the acylphosphonates to form a bicyclic hexahydropyrrolo[1,2-c]oxazol-1-ylphosphonates in good yield. No azomethine ylide formation was observed on the reaction of acylphosphonates with proline. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.05.091