Titanium-Mediated Cyclopropanation of Nitriles with Unsaturated Grignard Reagents: Application to the Synthesis of Constrained Lysine Derivatives

被引：5
|
作者：
Forcher, Gwenael [1 ]
Clousier, Nathalie [1 ]
Beauseigneur, Alice [1 ]
Setzer, Paul [1 ]
Boeda, Fabien [1 ]
Pearson-Long, Morwenna S. M. [1 ]
Karoyan, Philippe [2 ,3 ,4 ,5 ]
Szymoniak, Jan [6 ]
Bertus, Philippe [1 ]
机构：
[1] Univ Maine, CNRS, IMMM, UMR 6283, F-72085 Le Mans 9, France
[2] Univ Paris 06, Univ Sorbonne, LBM, F-75005 Paris, France
[3] PSL Res Univ, Dept Chim, Ecole Normale Super, F-75005 Paris, France
[4] CNRS, UMR 7203, LBM, F-75005 Paris, France
[5] GlaxoSmithKline, LBM, F-91140 Villebon Sur Yvette, France
[6] Univ Reims, CNRS, UMR 6229, F-51687 Reims 2, France
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 07期
关键词：
amino acids; cyclopropane; Grignard reaction; nitriles; titanium; ALPHA-AMINO-ACIDS; CATALYZED CYCLOPROPANATION; PRIMARY CYCLOPROPYLAMINES; SHORT ACCESS; PEPTIDOMIMETICS; CONSTRUCTION; COMBINATION; PEPTIDES; ANALOGS; ROUTE;
D O I：
10.1055/s-0034-1379978
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A comparative study of the titanium-mediated cyclopropanation of (benzyloxy)acetonitrile and Boc-protected cyanohydrin using unsaturated Grignard reagents (but-3-enyl- and pent-4-enylmagnesium bromides) is described. The best conditions to provide the cis and trans isomers of cyclopropylamines bearing unsaturation were identified and the alkene moiety was subjected to chemical modifications, as shown by the synthesis of orthogonally protected cis- and trans-2,3-methanolysine, cis-2,3-methanoornithine, and cis-2,3-methanohomolysine.
引用
收藏
页码：992 / 1006
页数：15
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