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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 13期

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

页码：4610 / 4616

页数：7

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