C3 versus C5 Regioselectivity in the Intramolecular Dehydrative Friedel–Crafts Alkylation of Indole C4-Tethered Carbinols

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

Described herein is a mild catalytic dehydrative Friedel-Crafts alkylation of 1,1-diarylalkanols─a challenging reaction with exceedingly rare previous success, presumably because the unfavorable steric hindrance around reactive centers and competitive E1 reaction. Executing in an intramolecular fashion benefiting from high nucleophilicity indole, we have successfully utilized this synthesizing 3,4-fused indoles. Interestingly, strategy could also be applied to access 4,5-fused indoles via modification tether connecting alcohol indole moieties.

Язык: Английский

Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4812 - 4819

Опубликована: Янв. 1, 2024

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols was established, which delivered various chiral pyrroloindoles in overall high yields with excellent diastereoselectivities and good enantioselectivities.

Язык: Английский