A general, Bronsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles

被引:204
作者
Wabnitz, TC [1 ]
Spencer, JB [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
关键词
D O I
10.1021/ol034596h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Strong Bronsted acids such as bis(trifluoromethariesulfon)imide catalyze the hetero-Michael addition of carbamates, alcohols, and thiols to alpha,beta-unsaturated ketones, alkylidene malonates, and acrylimides. Scope, reaction rates, and yields are superior to comparable Lewis acid-catalyzed processes.
引用
收藏
页码:2141 / 2144
页数:4
相关论文
共 61 条
[21]  
Juaristi E, 1999, CURR MED CHEM, V6, P983
[22]  
Juaristi E., 1997, ENANTIOSELECTIVE SYN
[23]  
Jung M. E., 1991, COMPREHENSIVE ORGANI, V4, P30
[24]   Transition metal-catalyzed addition of amines to acrylic acid derivatives. A high-throughput method for evaluating hydroamination of primary and secondary alkylamines [J].
Kawatsura, M ;
Hartwig, JF .
ORGANOMETALLICS, 2001, 20 (10) :1960-1964
[25]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094
[26]   Transition metal salts-catalyzed aza-Michael reactions of enones with carbamates [J].
Kobayashi, S ;
Kakumoto, K ;
Sugiura, M .
ORGANIC LETTERS, 2002, 4 (08) :1319-1322
[27]   Metal-catalyzed carbon-sulfur bond formation [J].
Kondo, T ;
Mitsudo, T .
CHEMICAL REVIEWS, 2000, 100 (08) :3205-3220
[28]   THE GAS-PHASE ACIDITIES OF VERY STRONG NEUTRAL BRONSTED ACIDS [J].
KOPPEL, IA ;
TAFT, RW ;
ANVIA, F ;
ZHU, SZ ;
HU, LQ ;
SUNG, KS ;
DESMARTEAU, DD ;
YAGUPOLSKII, LM ;
YAGUPOLSKII, YL ;
IGNATEV, NV ;
KONDRATENKO, NV ;
VOLKONSKII, AY ;
VLASOV, VM ;
NOTARIO, R ;
MARIA, PC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3047-3057
[29]  
KOSOKAWA T, 1989, CHEM LETT, P2001
[30]  
Krause N, 2001, SYNTHESIS-STUTTGART, P171