Chiral Brønsted Acid Catalyzed Enantioconvergent Synthesis of Chiral Tetrahydrocarbazoles with Allenylsilanes from Racemic Indolylmethanols
Shigenobu Umemiya, Kong Lingqi, Yuno Eto, Masahiro Terada
Abstract
Abstract An efficient method for the synthesis of chiral tetrahydrocarbazoles (THCs) containing an allene moiety is disclosed, which was established by an enantioconvergent substitution reaction catalyzed by a chiral phosphoric acid. Racemic indolylmethanols bearing the THC motif reacted with N-methylpyrrole in the presence of the SPINOL-derived chiral phosphoric acid to give the corresponding chiral THCs with allenylsilanes in good yields with high enantioselectivities.
Topics & Concepts
ChemistryMoietyPhosphoric acidAlleneOrganic chemistryCatalysisEnantioselective synthesisBrønsted–Lowry acid–base theoryStereochemistryCombinatorial chemistrySynthesis of Indole DerivativesAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality Synthesis