First Examples of Proline‐Catalyzed Domino Knoevenagel/Hetero‐Diels–Alder/Elimination Reactions | Zendy

Sabitha Gowravaram | Zendy; Fatima Narjis | Zendy; Reddy E. Venkata | Zendy; Yadav J. S. | Zendy

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First Examples of Proline‐Catalyzed Domino Knoevenagel/Hetero‐Diels–Alder/Elimination Reactions

Author(s) -

Sabitha Gowravaram,

Fatima Narjis,

Reddy E. Venkata,

Yadav J. S.

Publication year - 2005

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200505144

Subject(s) - knoevenagel condensation , chemistry , domino , catalysis , aldehyde , proline , organic chemistry , organocatalysis , diels–alder reaction , amino acid , biochemistry , enantioselective synthesis

A novel and efficient one‐pot synthesis of lactones (pyranones) has been achieved by domino Knoevenagel/hetero‐Diels–Alder/elimination reactions of O ‐ and N ‐prenyl aldehyde derivatives with Meldrum's acid in the presence of L ‐ or D , L ‐proline. The reaction proceeds cleanly at room temperature to afford cis ‐ or trans ‐fused products in good yields with high diastereoselectivity.

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