Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction

被引:113
作者
Courant, Thibaut [1 ]
Masson, Geraldine [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
关键词
alkylation; domino reactions; enamides; photoredox catalysis; radicals; VISIBLE-LIGHT PHOTOCATALYSIS; RADICAL CYCLIZATION REACTIONS; ORGANO-SOMO CATALYSIS; C-C; ENANTIOSELECTIVE SYNTHESIS; COORDINATION-COMPOUNDS; ASYMMETRIC ALKYLATION; REDUCTIVE ALKYLATION; ADDITION-REACTIONS; ALDEHYDES;
D O I
10.1002/chem.201103062
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Radical-polar crossover reaction: The photoredox-mediated alkylation of enamides with diethyl bromomalonate in the presence of alcohols has been developed. This multicomponent domino process affords β-alkylated α-carbamido ethers as stables imine surrogates in good to excellent yields under mild conditions (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:423 / 427
页数:5
相关论文
共 172 条
[1]   Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions [J].
Aelterman, W ;
De Kimpe, N ;
Tyvorskii, V ;
Kulinkovich, O .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :53-58
[2]  
Ahn JH, 1996, SYNLETT, P1224
[3]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[4]   The Holy Grail of Organocatalysis: Intermolecular α-Alkylation of Aldehydes [J].
Alba, Andrea-Nekane ;
Viciano, Monica ;
Rios, Ramon .
CHEMCATCHEM, 2009, 1 (04) :437-439
[5]  
Amatore M., 2009, Angew. Chem, V121, P5223
[6]   Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation [J].
Amatore, Muriel ;
Beeson, Teresa D. ;
Brown, Sean P. ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5121-5124
[7]  
Andrews R.S., 2010, ANGEW CHEM, V122, P7432
[8]   Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ORGANIC LETTERS, 2011, 13 (09) :2406-2409
[9]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[10]  
Andrews S. R., 2010, ANGEW CHEM, V122, P7432