Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

被引：8
作者：
Gagnot, Glwadys [1 ,2 ,3 ]
Hervin, Vincent [1 ,2 ]
Coutant, Eloi P. [1 ,2 ]
Desmons, Sarah [1 ,2 ]
Baatallah, Racha [1 ,2 ]
Monnot, Victor [1 ,2 ]
Janin, Yves L. [1 ,2 ]
机构：
[1] Inst Pasteur, Dept Biol Struct & Chim, Unite Chim & Biocatalyse, 28 Rue Dr Roux, F-75724 Paris 15, France
[2] CNRS, Unite Mixte Rech 3523, 28 Rue Dr Roux, F-75724 Paris 15, France
[3] Univ Paris 05, Sorbonne Paris Cite, 12 Rue Ecole Med, F-75006 Paris, France
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷
关键词：
alpha-amino ester; alpha-nitro esters; cerium ammonium nitrate; cycloaddition; gold(I) cyclization; ALIPHATIC NITRO-COMPOUNDS; KNOEVENAGEL CONDENSATION; GEMINAL DIACETATES; PROPARGYLIC AMIDES; DERIVATIVES; ALDEHYDES; ACIDS; 4H-1,2-BENZOXAZINES; NITROALKANES; CYCLIZATION;
D O I：
10.3762/bjoc.14.263
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report here on the use of ethyl nitroacetate as a glycine template to produce alpha-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into alpha-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing alpha-amino esters was achieved using gold(I) chemistry.
引用
收藏
页码：2846 / 2852
页数：7
相关论文
共 40 条
[1]  
Aggarwal VK, 1998, SYNLETT, P849
[2]   NEW ASPECTS IN THE HYDROGENOLYTIC OPENING OF 2-ISOXAZOLINES [J].
AURICCHIO, S ;
RICCA, A .
TETRAHEDRON, 1987, 43 (17) :3983-3986
[3]   Synthesis and reactivity of furoquinolines bearing an external methylene-bond: access to reduced and spirocyclic structures [J].
Bantreil, Xavier ;
Vaxelaire, Carine ;
Godet, Thomas ;
Parker, Evelyne ;
Sauer, Carole ;
Belmont, Philippe .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) :4831-4841
[4]   Click glycoconjugation of per-azido- and alkynyl-functionalized β-peptides built from aspartic acid [J].
Barra, Marielle ;
Roy, Olivier ;
Traikia, Mounir ;
Taillefumier, Claude .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) :2941-2955
[5]  
Bull R. J., 2009, PCT Patent Application, Patent No. [WO 2009/ 098455 A1, 2009/]
[6]   Isoxazoline derivatives from activated primary nitrocompounds and tertiary diamines [J].
Cecchi, L ;
De Sarlo, F ;
Machetti, F .
TETRAHEDRON LETTERS, 2005, 46 (46) :7877-7879
[7]   1,4-diazabicyclo[2.2.2]octane (DABCO) as an efficient reagent for the synthesis of isoxazole derivatives from primary nitro compounds and dipolarophiles: The role of the base [J].
Cecchi, Luca ;
De Sarlo, Francesco ;
Machetti, Fabrizio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4852-4860
[8]   Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate [J].
Coutant, Eloi P. ;
Hervin, Vincent ;
Gagnot, Glwadys ;
Ford, Candice ;
Baatallah, Racha ;
Janin, Yves L. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :2853-2860
[9]   1 Synthetic Routes to Coelenterazine and Other Imidazo[1,2-a]pyrazin-3-one Luciferins: Essential Tools for Bioluminescence-Based Investigations [J].
Coutant, Eloi P. ;
Janin, Yves L. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (48) :17158-17171
[10]  
DAUZONNE D, 1987, SYNTHESIS-STUTTGART, P399
1234