6533b82cfe1ef96bd128ed17

RESEARCH PRODUCT

Tandem Organocatalytic Cycloaromatization/Intramolecular Friedel-Crafts Alkylation Sequence for the Synthesis of Indolizinones and Pyrrolo-azepinone Derivatives.

Carlos Del PozoMaría Sánchez-rosellóSantos FusteroFernando Rabasa-alcañiz

subject

Tandem010405 organic chemistryStereochemistryChemistryIntramolecular forceOrganic Chemistry010402 general chemistry01 natural sciencesFriedel–Crafts reaction0104 chemical sciencesSequence (medicine)

description

The organocatalytic synthesis of indolizinones and pyrrolo-azepinones has been accomplished in a tandem fashion through a sequence that comprises initial cycloaromatization followed by intramolecular Friedel-Crafts alkylation. The process takes place under Bronsted acid catalysis, giving rise to final products in moderate to good yields. Attempts to carry out the tandem protocol in an enantioselective fashion were performed with chiral (R)-BINOL-derived N-triflyl phosphoramides. After initial optimization, the tandem process took place with moderate levels of enantioselectivity.

10.1021/acs.joc.9b01314https://pubmed.ncbi.nlm.nih.gov/31329441