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

• Published in: Tetrahedron Vol. 73; no. 30; pp. 4329 - 4334
• Main Authors: Subasi, N. Tuna, Yalcinkaya, Hatice, Demir, Ayhan S.
• Format: Journal Article
• Language: English
• 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

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...