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

共 50 条

[1] A general procedure for the asymmetric synthesis of 3-aryl-1,2,3,4-tetrahydroisoquinolines
Vicario, JL
Badía, D
Carrillo, L
Anakabe, E
TETRAHEDRON-ASYMMETRY, 2003, 14 (03) : 347 - 353
[2] A PRACTICAL SYNTHESIS OF 4-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
HARA, H
SHIRAI, R
HOSHINO, O
UMEZAWA, B
HETEROCYCLES, 1984, 21 : 696 - 696
[3] A facile synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines
Hu, Min
Guzzo, Peter R.
Zha, Congxiang
Nacro, Kassoum
Yang, Yuh-Lin
Hassler, Carla
Liu, Shuang
TETRAHEDRON LETTERS, 2012, 53 (07) : 846 - 848
[4] AN EFFICIENT SYNTHESIS OF 4-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
NARASIMHAN, NS
PATIL, PA
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) : 191 - 192
[5] AN EFFICIENT SYNTHESIS OF 4-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
MILLER, RB
SVOBODA, JJ
SYNTHETIC COMMUNICATIONS, 1994, 24 (08) : 1187 - 1193
[6] NEW METHOD FOR SYNTHESIS OF 2-ACYL-1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
MOLLOV, NM
VENKOV, AP
SYNTHESIS-STUTTGART, 1978, (01): : 62 - 63
[7] Stereocontrolled metalloenamine alkylations:: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines
Vicario, JL
Badía, D
Domínguez, E
Carrillo, L
TETRAHEDRON-ASYMMETRY, 2000, 11 (18) : 3779 - 3788
[8] THE SYNTHESIS OF 8-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
HARA, H
HOSHINO, O
UMEZAWA, B
HETEROCYCLES, 1981, 15 (02) : 911 - 914
[9] A NEW SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
BOBBITT, JM
KHANNA, KL
KIELY, JM
CHEMISTRY & INDUSTRY, 1964, (47) : 1950 - 1951
[10] SYNTHESIS OF NEW 4-ARYL-8-HETEROARYL-2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINES
ZARAKACZIAN, E
DEAK, G
ACTA CHIMICA HUNGARICA-MODELS IN CHEMISTRY, 1989, 126 (05): : 723 - 732

← 1 2 3 4 5 →