title: A New General Method for the Asymmetric Synthesis of 4-Alkyl-3-aryl-1,2,3,4-tetrahydroisoquinolines.
abstract: A highly enantioselective method for the synthesis of 4-alkyl substituted 1,2,3,4-tetrahydroisoquinolines is reported. The key step relies on the asymmetric synthesis of alpha-alkylarylacetic acids by alkylation of their corresponding amides employing (S,S)-(+)-pseudoephedrine as chiral inductor. Subsequent Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization affords the title compounds in excellent yields and enantioselectivities.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad del Pais Vasco, P.O. Box 644, 48080 Bilbao, Spain.
authors.forename: Jose L.
authors.initials: JL
authors.lastname: Vicario
authors.forename: Dolores
authors.initials: D
authors.lastname: Badía
authors.forename: Esther
authors.initials: E
authors.lastname: Domínguez
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo