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

被引:49
作者
Vicario, JL [1 ]
Badía, D [1 ]
Domínguez, E [1 ]
Carrillo, L [1 ]
机构
[1] Univ Basque Country, Dept Quim Organ, Fac Ciencias, E-48080 Bilbao, Spain
关键词
D O I
10.1021/jo982008l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4610 / 4616
页数:7
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