Bi(OTf)3-catalyzed three-component synthesis of α-amino acid derivatives

被引:19
作者
Schneider, Angelika E. [1 ]
Beisel, Tamara [1 ]
Shemet, Andrej [1 ]
Manolikakes, Georg [1 ]
机构
[1] Goethe Univ Frankfurt, Dept Organ Chem & Chem Biol, D-60054 Frankfurt, Germany
关键词
N-ACYLIMINIUM IONS; BISMUTH TRIFLATE; ONE-POT; PHARMACOKINETIC PROPERTIES; ANTIBACTERIAL ACTIVITY; ASYMMETRIC-SYNTHESIS; LEWIS-ACID; EFFICIENT; ALLYLATION; ESTERS;
D O I
10.1039/c4ob00265b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient Bi(OTf)(3)-catalyzed multicomponent synthesis of arylglycines from readily available starting materials is described. The reaction proceeds under mild conditions and provides a general route to various N-protected arylglycines.
引用
收藏
页码:2356 / 2359
页数:4
相关论文
共 58 条
[1]  
[Anonymous], ANTIMICROBIALS NEW O
[2]   NEW SYNTHESIS OF ALPHA-AMINO-ACIDS .3. AMIDOALKYLATION OF ACTIVE METHYLENE-COMPOUNDS WITH GLYOXYLIC-ACID DERIVATIVES [J].
BENISHAI, D ;
ALTMAN, J ;
BERNSTEIN, Z ;
PELED, N .
TETRAHEDRON, 1978, 34 (04) :467-473
[3]   Applications of bismuth(III) compounds in organic synthesis [J].
Bothwell, Jason M. ;
Krabbe, Scott W. ;
Mohan, Ram S. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4649-4707
[4]   One-pot synthesis of aryl glycines and other unnatural amino acids from serine derivatives [J].
Boto, A ;
Hernández, R ;
Montoya, A ;
Suárez, E .
TETRAHEDRON LETTERS, 2002, 43 (46) :8269-8272
[5]   TEICOPLANIN - A REVIEW OF ITS ANTIBACTERIAL ACTIVITY, PHARMACOKINETIC PROPERTIES AND THERAPEUTIC POTENTIAL [J].
CAMPOLIRICHARDS, DM ;
BROGDEN, RN ;
FAULDS, D .
DRUGS, 1990, 40 (03) :449-486
[6]   Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction [J].
Candeias, Nuno R. ;
Montalbano, Francesco ;
Cal, Pedro M. S. D. ;
Gois, Pedro M. P. .
CHEMICAL REVIEWS, 2010, 110 (10) :6169-6193
[7]   The direct catalytic asymmetric Mannich reaction [J].
Córdova, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112
[8]   Catalytic α-Allylation of Unprotected Amino Acid Esters [J].
Fang, Ping ;
Chaulagain, Mani Raj ;
Aron, Zachary D. .
ORGANIC LETTERS, 2012, 14 (08) :2130-2133
[9]   Bismuth(III) triflate in organic synthesis [J].
Gaspard-Iloughmane, H ;
Le Roux, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) :2517-2532
[10]   One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase [J].
Grundmann, Peter ;
Fessner, Wolf-Dieter .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) :1729-1735