A new general method for the asymmetric synthesis of 4-alkyl-3-aryl-1,2,3,4-tetrahydroisoquinolines

Authors
Vicario, JL Badia, D Dominguez, E Carrillo, L
Citation
Jl. Vicario et al., A new general method for the asymmetric synthesis of 4-alkyl-3-aryl-1,2,3,4-tetrahydroisoquinolines, J ORG CHEM, 64(13), 1999, pp. 4610-4616
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
13
Year of publication
1999
Pages
4610 - 4616
Database
ISI
SICI code
0022-3263(19990625)64:13<4610:ANGMFT>2.0.ZU;2-F
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 asym metric synthesis of alpha-alkylarylacetic acids by alkylation of their corr esponding amides employing (S,S)-(+)-pseudoephedrine as chiral inductor. Su bsequent Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization affords the title compounds in excellent yield s and enantioselectivities.