Enantioselective synthesis of aroylalanine derivatives

被引：30

作者：

Lygo, B ^{[1
]}

Andrews, BI ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(03)01017-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper we report the development of a highly enantioselective method for the synthesis of aroylalanines. The approach described employs a protected 2-amino-4-bromopent-4-enoic acid, generated via the asymmetric phase-transfer catalyzed alkylation of a glycine imine, as a key intermediate. Suzuki coupling with an aryl boronic acid followed by ozonolysis of the resulting styrene provides efficient access to the aroylalanine derivatives. The utility of this methodology is illustrated by the synthesis Of L-kynurenine along with several aroylalanine inhibitors of the kynurenine pathway. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4499 / 4502

页数：4

共 75 条

[1] Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate
Arai, S
Tsuji, R
Nishida, A
[J]. TETRAHEDRON LETTERS, 2002, 43 (52) : 9535 - 9537
[2] The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)
Belokon', YN
Davies, RG
Fuentes, JA
North, M
Parsons, T
[J]. TETRAHEDRON LETTERS, 2001, 42 (45) : 8093 - 8096
[3] Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions
Belokon, YN
North, M
Churkina, TD
Ikonnikov, NS
Maleev, VI
[J]. TETRAHEDRON, 2001, 57 (13) : 2491 - 2498
[4] Belokon YN, 2001, ANGEW CHEM INT EDIT, V40, P1948, DOI 10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.3.CO
[5] 2-F
[6] Synthesis of anisolylated aspartyl and glutamyl tripeptides
Berree, F
Chang, KY
Cobas, A
Rapoport, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 715 - 721
[7] Studies on the total synthesis of RP 66453: Synthesis of fully functionalized 15-membered biaryl-containing macrocycle
Boisnard, S
Carbonnelle, AC
Zhu, JP
[J]. ORGANIC LETTERS, 2001, 3 (13) : 2061 - 2064
[8] NEW SYNTHESES OF ALPHA-AMINO-ACIDS BASED ON N-ACYLIMINO ACETATES
BRETSCHNEIDER, T
MILTZ, W
MUNSTER, P
STEGLICH, W
[J]. TETRAHEDRON, 1988, 44 (17) : 5403 - 5414
[9] Inhibition of nNOS activity in rat brain by synthetic kynurenines:: Structure-activity dependence
Camacho, E
León, J
Carrión, A
Entrena, A
Escames, G
Khaldy, H
Acuña-Castroviejo, D
Gallo, MA
Espinosa, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (02) : 263 - 274
[10] Palladium-catalyzed allylic alkylation of tert-butyl(diphylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions
Chen, GS
Deng, YJ
Gong, LZ
Mi, AQ
Cui, X
Jiang, YZ
Choi, MCK
Chan, ASC
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1567 - 1571

← 1 2 3 4 5 6 7 8 →