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
[111]  
Melchiorre P., 2009, ANGEW CHEM, V121, P1386
[112]   Asymmetric aminocatalysis - Gold rush in organic chemistry [J].
Melchiorre, Paolo ;
Marigo, Mauro ;
Carlone, Armando ;
Bartoli, Giuseppe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6138-6171
[113]   Light in Aminocatalysis: The Asymmetric Intermolecular α-Alkylation of Aldehydes [J].
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1360-1363
[114]   Stereoselective syntheses of the octahydropyrano[2,3-b]pyridine DE core of 'Upenamide via a stannous chloride-induced deacetalisation-cyclisation procedure [J].
Menard-Moyon, Cecilia ;
Taylor, Richard J. K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (22) :3698-3706
[115]   Nucleophilic α-Arylation and α-Alkylation of Ketones by Polarity Inversion of N-Alkoxyenamines: Entry to the Umpolung Reaction at the α-Carbon Position of Carbonyl Compounds [J].
Miyoshi, Tetsuya ;
Miyakawa, Takayuki ;
Ueda, Masafumi ;
Miyata, Okiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (04) :928-931
[116]   Asymmetric enamine catalysis [J].
Mukherjee, Santanu ;
Yang, Jung Woon ;
Hoffmann, Sebastian ;
List, Benjamin .
CHEMICAL REVIEWS, 2007, 107 (12) :5471-5569
[117]   PALLADIUM(0)-CATALYZED REARRANGEMENT OF N-ALLYLENAMINES - SYNTHESIS OF DELTA,EPSILON-UNSATURATED IMINES AND GAMMA,DELTA-UNSATURATED CARBONYL-COMPOUNDS [J].
MURAHASHI, S ;
MAKABE, Y ;
KUNITA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4489-4495
[118]   Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis [J].
Nagib, David A. ;
Scott, Mark E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10875-+
[119]   α-alkylation of ketones by addition of zinc enamides to unactivated olefins [J].
Nakamura, M ;
Hatakeyama, T ;
Nakamura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11820-11825
[120]   ADDITION-REACTIONS OF CATION RADICALS OF NITROALKANES TO OLEFINIC COMPOUNDS BY THE USE OF MANGANESE(III) 2-PYRIDINECARBOXYLATE [J].
NARASAKA, K ;
IWAKURA, K ;
OKAUCHI, T .
CHEMISTRY LETTERS, 1991, (03) :423-426