Highly diastereoselective conjugate addition of aryllithium to chiral β-nitrostyrene derivative:: An application to the asymmetric synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline

被引：5

作者：

Asami, Masatoshi ^{[1
]}

Taketoshi, Ayako ^{[1
]}

Miyoshi, Keita ^{[1
]}

Hoshino, Hayato ^{[1
]}

Sakakibara, Kazuhisa ^{[1
]}

机构：

[1] Yokohama Natl Univ, Grad Sch Engn, Dept Adv Mat Chem, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

来源：

CHEMISTRY LETTERS | 2007年 / 36卷 / 01期

关键词：

D O I：

10.1246/cl.2007.64

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly diastereoselective conjugate addition of aryllithium to beta-nitrostyrene derivative, having chiral acetal moiety derived from (S,S)- 1,2-bis(1-hydroxypropyl)benzene, was achieved. The adduct was transformed to 4-aryl-1,2,3,4-tetrahydroisoquinoline in high enantiomeric excess (ee).

引用

页码：64 / 65

页数：2

共 50 条

[1] Oxazoline as a useful tool in organic synthesis:: preparation of 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid skeleton
Seijas, JA
Vázquez-Tato, MP
Martínez, MM
Pizzolatti, MG
TETRAHEDRON LETTERS, 2005, 46 (35) : 5827 - 5830
[2] Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures
Nery, MS
Ribeiro, RP
Lopes, CC
Lopes, RSC
SYNTHESIS-STUTTGART, 2003, (02): : 272 - 276
[3] SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, AND 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE AS DOPAMINE RECEPTOR LIGANDS
CHARIFSON, PS
WYRICK, SD
HOFFMAN, AJ
SIMMONS, RMA
BOWEN, JP
MCDOUGALD, DL
MAILMAN, RB
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) : 1941 - 1946
[4] NOVEL SYNTHESIS OF 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE
SCHWAN, TJ
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (05) : 839 - &
[5] Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol
Geng Xu
Chinese Chemical Letters, 2010, 21 (03) : 309 - 311
[6] Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol
Xu, Geng
Liu, Zhan Zhu
CHINESE CHEMICAL LETTERS, 2010, 21 (03) : 309 - 311
[7] A PRACTICAL SYNTHESIS OF 4-(3',4'-DIHYDROXYLPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE
ZHAO, WM
WAN, XY
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1995, 27 (04) : 513 - 516
[8] A PRACTICAL SYNTHESIS OF 4-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
HARA, H
SHIRAI, R
HOSHINO, O
UMEZAWA, B
HETEROCYCLES, 1984, 21 : 696 - 696
[9] 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
[10] 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

← 1 2 3 4 5 →