Synthesis of β-fluoro-β-proline

被引：21
作者：
Yarmolchuk, Vladimir S.
Mykhailiuk, Pavel K. [1 ]
Komarov, Igor V.
机构：
[1] Enamine Ltd, UA-01103 Kiev, Ukraine
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 12期
关键词：
Fluorine; beta-Amino acids; Proline; Drug design; DIPOLAR CYCLOADDITION REACTIONS; AMINO ACID-DERIVATIVES; ASYMMETRIC-SYNTHESIS; MEDICINAL CHEMISTRY; PYRROLIDINE; PHARMACEUTICALS; AGONISTS; ANALOGS; ETHERS;
D O I：
10.1016/j.tetlet.2011.01.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic strategy towards the novel amino acid beta-fluoro-beta-proline, a fluorinated analogue of beta-proline, is elaborated. The synthesis commences from commercially available methyl 2-fluoroacrylate and involves three steps. The overall yield of beta-fluoro-beta-proline is 57%. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1300 / 1302
页数：3
相关论文
共 48 条
[1]   Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].
Begue, Jean-Pierre ;
Bonnet-Delpon, Daniele .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012
[2]   Fluorine in medicinal chemistry [J].
Böhm, HJ ;
Banner, D ;
Bendels, S ;
Kansy, M ;
Kuhn, B ;
Müller, K ;
Obst-Sander, U ;
Stahl, M .
CHEMBIOCHEM, 2004, 5 (05) :637-643
[3]   First 1,3-dipolar cycloaddition of azomethine ylides with (E)-ethyl 3-fluoroacrylate:: Regio- and stereoselective synthesis of enantiopure fluorinated prolines [J].
Bonini, BF ;
Boschi, F ;
Franchini, MC ;
Fochi, M ;
Fini, F ;
Mazzanti, A ;
Ricci, A .
SYNLETT, 2006, (04) :543-546
[4]   Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].
Coldham, I ;
Hufton, R .
CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809
[5]   POLY(ETHYLENIMINES) WITH ALTERNATIVE (ALKYLAMINO)PYRIDINES AS NUCLEOPHILIC CATALYSTS [J].
DELANEY, EJ ;
WOOD, LE ;
KLOTZ, IM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) :799-807
[6]  
DENG Y, 2007, Patent No. 2007097937
[7]   Diastereoselective synthesis of fluorinated, seven-membered β-amino acid derivatives via ring-closing metathesis [J].
Fustero, S ;
Bartolomé, A ;
Sanz-Cervera, JF ;
Sánchez-Roselló, M ;
Soler, JG ;
de Arellano, CR ;
Fuentes, AS .
ORGANIC LETTERS, 2003, 5 (14) :2523-2526
[8]   Asymmetric synthesis of fluorinated cyclic β-amino acid derivatives through cross metathesis [J].
Fustero, Santos ;
Sanchez-Rosello, Maria ;
Sanz-Cervera, Juan F. ;
Acena, Jose Luis ;
del Pozo, Carlos ;
Fernandez, Begona ;
Bartolome, Ana ;
Asensio, Amparo .
ORGANIC LETTERS, 2006, 8 (20) :4633-4636
[9]   Trifluoromethyl-substituted cyclopropanes [J].
Grygorenko, Oleksandr O. ;
Artamonov, Oleksiy S. ;
Komarov, Igor V. ;
Mykhailiuk, Pavel K. .
TETRAHEDRON, 2011, 67 (05) :803-823
[10]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
12345