Premium
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.