Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• [3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative

• in governing the endo stereocontrol. Keywords: endo-Diels–Alder stereocontrol; 2-formylpyrrole; intramolecular Heck arylation reaction; non-covalent interactions; pyrroloindoles; pyrroloisoindoles; Introduction Pyrrolizines [1][2] and pyrrolizidines [3][4], abundant in nature [4][5], are among the

• nitrogen atom of the heterocycle. Since it is not clear what factors favor this relevant selectivity, the geometry and energy of the TSs were calculated for some of the diene–dienophile pairs depicted in Table 2 (vide infra). Cyclization via an intramolecular Heck arylation reaction Before attempting the