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. https://doi.org/10.3762/bjoc.16.113

Supporting Information

Appendix 1: Energies and coefficients of the Frontier Molecular Orbitals [HF/6-31G(d,p)] of dienes 8b, 8c and 8g, and dienophile 7c. Appendix 2: Relative zero point-corrected energies of the SCs, TSs, and ADs located on the potential surfaces of the Diels–Alder reactions of dienes 8b, 8c, 8g, 8j, 16a, and 18a, and dienophiles 7b,c. Appendix 3: X-ray crystallographic structures of 9m and 10m. Appendix 4: M06-2X/6-31+G(d,p) relative Gibbs free energies (kcal/mol) of the stationary points in the Diels–Alder cycloadditions of dienes 8b, 8c, 8g, 8j, 16a, and 18a, and dienophiles 7b,c. Appendix 5: Calculation [M06-2X/6-31+G(d,p)] of Z-matrices of the optimized geometries of the SCs, TSs, and ADs of the Diels–Alder cycloadditions of dienes 8b, 8c, 8g, 8j, 16a, and 18a, and dienophiles 7b,c. Appendix 6: Calculation [M06-2X/6-31+G(d,p)] of the NCIs, including distances, angles and contact type from the ZPE-corrected geometries of the endo TSs of the Diels–Alder reactions of dienes 8b, 8c, 8g, 8j and 18a and dienophiles 7b,c. Appendix 7: Experimental section. Appendix 8: 1H and 13C NMR spectra for all new compounds.

Supporting Information File 1: Experimental and analytical data, X-ray crystallographic structures, NMR-spectra and all calculated data.
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