Solvent-free synthesis of unsaturated amino esters in a ball-mill

被引：37

作者：

Baron, Alice

Martinez, Jean

Lamaty, Frederic ^{[1
]}

机构：

[1] Univ Montpellier I, CNRS, Inst Biomol Max Mousseron, UMR 5247, F-34095 Montpellier 05, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 48期

关键词：

Ball-mill; Solvent-free; Amino acid; Horner-Wadsworth-Emmons; Olefination; Dehydroalanine; Carbonate base; Phosphonate; WADSWORTH-EMMONS REACTION; SOLID-STATE; HECK REACTION; ACID; MICROWAVE; PEPTIDES;

D O I：

10.1016/j.tetlet.2010.09.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ball-milling technique was used under solvent-free conditions to perform a Horner-Wadsworth-Emmons reaction in the presence of a mild carbonate base. Starting from a phosphonate-substituted glycine, this method gave access to Boc-protected unsaturated amino esters in excellent yield and selectivity in many cases. The scope of the reaction was delineated. (C) 2010 Elsevier Ltd. All rights reserved.

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页码：6246 / 6249

页数：4

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共 41 条

[1] Solvent-free Horner-Wadsworth-Emmons reaction using DBU [J].

Ando, Kaori ;

Yamada, Kyohei .

TETRAHEDRON LETTERS, 2010, 51 (25) :3297-3299

[2] Mechanically induced solid-state generation of phosphorus ylides and the solvent-free Wittig reaction [J].

Balema, VP ;

Wiench, JW ;

Pruski, M ;

Pecharsky, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6244-6245

[3] Solvent-free and time-efficient Suzuki-Miyaura reaction in a ball mill: the solid reagent system KF-Al2O3 under inspection [J].

Bernhardt, Franziska ;

Trotzki, Ronald ;

Szuppa, Tony ;

Stolle, Achim ;

Ondruschka, Bernd .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6

[4] Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation [J].

Bruckmann, Angelika ;

Krebs, Anke ;

Bolm, Carsten .

GREEN CHEMISTRY, 2008, 10 (11) :1131-1141

[5] Solvent-free synthesis of nitrones in a ball-mill [J].

Colacino, Evelina ;

Nun, Pierrick ;

Colacino, Francesco Maria ;

Martinez, Jean ;

Lamaty, Frederic .

TETRAHEDRON, 2008, 64 (23) :5569-5576

[6] 2-Trimethylsilylethanesulfonyl (SES) versus tosyl (Ts) protecting group in the preparation of nitrogen-containing five-membered rings. A novel route for the synthesis of substituted pyrrolines and pyrrolidines [J].

Declerck, Valerie ;

Allouchi, Hassan ;

Martinez, Jean ;

Lamaty, Frederic .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1518-1521

[7] A microwave-assisted heck reaction in poly(ethylene glycol) for the synthesis of benzazepines [J].

Declerck, Valerie ;

Ribiere, Patrice ;

Nedellec, Yannig ;

Allouchi, Hassan ;

Martinez, Jean ;

Lamaty, Frederic .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) :201-208

[8] Solvent-Free Synthesis of Peptides [J].

Declerck, Valerie ;

Nun, Pierrick ;

Martinez, Jean ;

Lamaty, Frederic .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9318-9321

[9] Selective [3+2] Huisgen Cycloaddition. Synthesis of Trans-Disubstituted Triazolodiazepines from Aza-Baylis-Hillman Adducts [J].

Declerck, Valerie ;

Toupet, Loic ;

Martinez, Jean ;

Lamaty, Frederic .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) :2004-2007

[10] Solvent-free Sonogashira coupling reaction via high speed ball milling [J].

Fulmer, Dennis A. ;

Shearouse, William C. ;

Medonza, Shareika T. ;

Mack, James .

GREEN CHEMISTRY, 2009, 11 (11) :1821-1825

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