Two classes of enantiopure molecular scaffolds were prepared, whose lactam structure formally derives from the coupling between tartaric acid and beta- or gamma-ketoamines. We labelled these compounds as 8-exo and 9-exo BTKa, indicating the lactam size (8- and 9-membered ring, respectively). Starting from beta- and gamma-nitroketones, the synthesis involves the ketal formation by (R,R)-dimethyl tartrate. The subsequent amide bond formation occurs during the hydrogenation of the nitro group over Raney-Ni and no expected open chain amine was observed.

Synthesis of New Molecular Scaffolds: 3-Aza-7,9-Dioxa-Bicyclo[4.2.1]Nonane (8-exo BTKa) and 3-Aza-8,10-Dioxa-Bicyclo[5.2.1]Decane (9-exo BTKa) Carboxylic Acids / D. SCARPI; D. STRANGES; L. CECCHI; A. GUARNA. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 60:(2004), pp. 2583-2591. [10.1016/j.tet.2004.01.039]

Synthesis of New Molecular Scaffolds: 3-Aza-7,9-Dioxa-Bicyclo[4.2.1]Nonane (8-exo BTKa) and 3-Aza-8,10-Dioxa-Bicyclo[5.2.1]Decane (9-exo BTKa) Carboxylic Acids

SCARPI, DINA;GUARNA, ANTONIO
2004

Abstract

Two classes of enantiopure molecular scaffolds were prepared, whose lactam structure formally derives from the coupling between tartaric acid and beta- or gamma-ketoamines. We labelled these compounds as 8-exo and 9-exo BTKa, indicating the lactam size (8- and 9-membered ring, respectively). Starting from beta- and gamma-nitroketones, the synthesis involves the ketal formation by (R,R)-dimethyl tartrate. The subsequent amide bond formation occurs during the hydrogenation of the nitro group over Raney-Ni and no expected open chain amine was observed.
2004
60
2583
2591
D. SCARPI; D. STRANGES; L. CECCHI; A. GUARNA
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/211341
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