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
[71]  
Hao J, 2001, SYNLETT, P1443
[72]   Eosin Y Catalyzed Visible Light Oxidative C-C and C-P bond Formation [J].
Hari, Durga Prasad ;
Koenig, Burkhard .
ORGANIC LETTERS, 2011, 13 (15) :3852-3855
[73]   Alkylation of magnesium enamide with alkyl chlorides and fluorides [J].
Hatakeyama, T ;
Ito, S ;
Nakamura, M ;
Nakamura, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14192-14193
[74]  
Heaney H., 1991, COMPREHENSIVE ORGANI, V2, P733
[75]  
HEISZWOLF GJ, 1970, RECL TRAV CHIM PAY-B, V89, P1217
[76]  
Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047
[77]   PALLADIUM-CATALYZED ASYMMETRIC ALLYLATIONS OF ALDEHYDES VIA (S)-PROLINE ALLYL ESTER ENAMINES [J].
HIROI, K ;
ABE, J ;
SUYA, K ;
SATO, S .
TETRAHEDRON LETTERS, 1989, 30 (12) :1543-1546
[78]   ASYMMETRIC INDUCTION REACTIONS .5. THE PALLADIUM-CATALYZED ASYMMETRIC ALPHA-ALLYLATIONS OF CARBONYL-COMPOUNDS WITH CHIRAL ALLYL ESTERS VIA ENAMINES AND IMINES [J].
HIROI, K ;
ABE, J ;
SUYA, K ;
SATO, S ;
KOYAMA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :203-213
[79]   PALLADIUM CATALYZED ANNULATION REACTION USING A BIFUNCTIONAL ALLYLIC ALKYLATING AGENT [J].
HUANG, YJ ;
LU, XY .
TETRAHEDRON LETTERS, 1988, 29 (44) :5663-5664
[80]   Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis [J].
Ibrahem, I ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1952-1956