ABSTRACT
A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective SN2-type ring-opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%).
Subject(s)
Aziridines/chemistry , Hydrocarbons, Halogenated/chemistry , Indoles/chemistry , Indoles/chemical synthesis , Catalysis , Cyclization , Molecular Structure , StereoisomerismABSTRACT
A simple strategy for the synthesis of chiral α,ß-diamino- and α-amino,ß-hydroxy ester derivatives in high yields with moderate to high ee has been developed via asymmetric imino-aldol and aldol reactions, respectively, starting from protected aminoesters employing memory of chirality concept for chiral induction. This strategy has been extended for the enantioselective synthesis of aziridines (ee up to 92%). The absolute configuration of the imino-aldol adducts has been determined. The stereochemical outcome of the products has been explained by a suitable mechanism and supported by computational studies.
Subject(s)
Amino Acids, Diamino/chemistry , Aziridines/chemistry , Aziridines/chemical synthesis , Imines/chemistry , Amino Acids, Diamino/chemical synthesis , Catalysis , Computer Simulation , Esters , Molecular Structure , StereoisomerismABSTRACT
A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and stereoselectivity (ee and de up to >99%).
