β-C(sp2)-H alkylation of enamides using xanthate chemistry

被引:18
作者
Bertho, Sylvain [1 ]
Dondasse, Ismael [1 ]
Retailleau, Pascal [2 ]
Nicolas, Cyril [1 ]
Gillaizeau, Isabelle [1 ]
机构
[1] Univ Orleans, Inst Organ & Analyt Chem, CNRS, ICOA,UMR 7311, Rue Chartres, F-45100 Orleans, France
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
RADICAL TRANSFER; FUNCTIONALIZATION; ARYLDIAZOACETATES; ALKENYLATION; ALKALOIDS; ENAMINES;
D O I
10.1039/d0nj01209b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Access to the gamma-amino-beta,gamma-unsaturated acyl scaffold was established by applying xanthate chemistry to enamides. This original beta-C(sp(2))-H alkylation is regioselective and exhibits broad substrate scope and good functional group tolerance. The large availability of xanthates is advantageous to the scope of the reaction which combines a radical process and a polar reaction.
引用
收藏
页码:7129 / 7141
页数:13
相关论文
共 52 条
[1]  
Anker T., 2013, Chem. Eur. J, V19, P1858
[2]   Enamide Derivatives: Versatile Building Blocks for Highly Functionalized α,β-Substituted Amines [J].
Bernadat, Guillaume ;
Masson, Geraldine .
SYNLETT, 2014, 25 (20) :2842-2867
[3]   Regio- and Stereoselective Iron-Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent [J].
Bertho, Sylvain ;
Rey-Rodriguez, Romain ;
Colas, Cyril ;
Retailleau, Pascal ;
Gillaizeau, Isabelle .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (70) :17674-17677
[4]   Copper-catalyzed olefinic C-H difluoroacetylation of enamides [J].
Caillot, Gilles ;
Dufour, Jeremy ;
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Grimaud, Laurence ;
Pannecoucke, Xavier ;
Gillaizeau, Isabelle .
CHEMICAL COMMUNICATIONS, 2014, 50 (44) :5887-5890
[5]   Identification of deoxymiroestrol as the actual rejuvenating principle of "Kwao Keur", Pueraria mirifica.: The known miroestrol may be an artifact [J].
Chansakaow, S ;
Ishikawa, T ;
Seki, H ;
Sekine, K ;
Okada, M ;
Chaichantipyuth, C .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (02) :173-175
[6]   A new approach to cyclohexenes and related structures [J].
Cholleton, N ;
Gauthier-Gillaizeau, I ;
Six, Y ;
Zard, SZ .
CHEMICAL COMMUNICATIONS, 2000, (07) :535-536
[7]   Recent Advances in Radical-Initiated C(sp3)-H Bond Oxidative Functionalization of Alkyl Nitriles [J].
Chu, Xue-Qiang ;
Ge, Danhua ;
Shen, Zhi-Liang ;
Loh, Teck-Peng .
ACS CATALYSIS, 2018, 8 (01) :258-271
[8]   Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction [J].
Courant, Thibaut ;
Masson, Geraldine .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) :423-427
[9]   GROUP TRANSFER ADDITION-REACTIONS OF METHYL(PHENYLSELENO)MALONONITRILE TO ALKENES [J].
CURRAN, DP ;
EICHENBERGER, E ;
COLLIS, M ;
ROEPEL, MG ;
THOMA, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4279-4288
[10]   Copper-Catalyzed Oxidative Alkylation of Vinylic Cβ-H of Enamides with Cyclic Ethers [J].
Ding, R. ;
Lu, Wang-Gang ;
Ci, Hao ;
Mao, Yue-Yuan ;
Liu, Lei .
CHEMISTRYSELECT, 2019, 4 (23) :6954-6957