Asymmetric synthesis of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives

被引:14
作者
Alezra, V
Bonin, M
Micouin, L
Husson, HP
机构
[1] CNRS, Chim Therapeut Lab, F-75270 Paris 06, France
[2] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris, France
关键词
D O I
10.1016/S0040-4039(01)00075-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new route towards the asymmetric preparation of quaternary 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives has been developed. The key step involves an intramolecular Pictet-Spengler reaction of an oxazolidino ester. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2111 / 2113
页数:3
相关论文
共 10 条
[1]   Asymmetric functionalization of a chiral non-racemic oxazolidine ester enolate. A new route towards the preparation of quaternary serine esters [J].
Alezra, V ;
Bonin, M ;
Chiaroni, A ;
Micouin, L ;
Riche, C ;
Husson, HP .
TETRAHEDRON LETTERS, 2000, 41 (11) :1737-1740
[2]   A facile and highly stereoselective approach to a polycyclic isoindolinone ring system via an N-acyliminium ion cyclization reaction [J].
Allin, SM ;
Northfield, CJ ;
Page, MI ;
Slawin, AMZ .
TETRAHEDRON LETTERS, 1998, 39 (27) :4905-4908
[3]  
BAJGROWICZ J, 1986, HETEROCYCLES, V24, P2165
[4]  
Chinchilla R, 1999, SYNTHESIS-STUTTGART, P704
[5]   Towards control of χ-space:: Conformationally constrained analogues of Phe, Tyr, Trp and His [J].
Gibson, SE ;
Guillo, N ;
Tozer, MJ .
TETRAHEDRON, 1999, 55 (03) :585-615
[6]  
LISKAMP RMJ, 1994, RECL TRAV CHIM PAY B, V113, P1
[7]  
Ma DW, 1998, BIOORG MED CHEM LETT, V8, P2447
[8]   Affinity and selectivity of matrix metalloproteinase inhibitors: A chemometrical study from the perspective of ligands and proteins [J].
Matter, H ;
Schwab, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (22) :4506-4523
[9]   Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary delta opioid antagonist activity [J].
Salvadori, S ;
Balboni, G ;
Guerrini, R ;
Tomatis, R ;
Bianchi, C ;
Bryant, SD ;
Cooper, PS ;
Lazarus, LH .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (19) :3100-3108
[10]  
SEEBACH D, 1989, LIEBIGS ANN CHEM, P1215