An intramolecular oxo Diels–Alder approach to 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4- c]pyrrole-4-carboxylic acid ethyl esters

• Published in: Tetrahedron Vol. 59; no. 45; pp. 8955 - 8961
• Main Authors: Murray, William V, Mishra, Pranab K, Turchi, Ignatius J, Sawicka, Dorota, Maden, Amy, Sun, Sengen
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.11.2003; Elsevier
• Subjects: Chemistry; Chemistry, Organic; diastereoselective synthesis; Diels–Alder; Physical Sciences; pyrrolidine templates; Science & Technology; pyrrolidine templates; Diels–Alder; diastereoselective synthesis; ENANTIOPURE; SIDE-CHAIN FUNCTIONALITY; AMINO-ACIDS; Diels-Alder; PEPTIDE BACKBONE GEOMETRY; TRIENES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2003.04.007

The diastereoselective synthesis of a series of 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4- c]pyrrole-4-carboxylic acid ethyl esters via an oxo Diels–Alder reaction is described. Ab initio calculations predicted the products of the exo cycloaddition to be the thermodynamic products while the products resulting from the endo cycloaddition were predicted to be the kinetic products. The calculations were born out by experimental data. The diastereoselective synthesis of a series of 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3-4- c]pyrrole-4-carboxylic acid ethyl esters via an oxo Diels–Alder reaction is described. Ab initio calculations predicted the exo cycloaddition to yield the thermodynamic product and the endo addition to afford the kinetic product. The predictions were born out experimentally.