Rhodium-catalyzed asymmetric conjugate alkynylation of nitroalkenes

被引:32
作者
Nishimura, Takahiro [1 ]
Sawano, Takahiro [1 ]
Tokuji, Sumito [1 ]
Hayashi, Tamio [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
关键词
ENANTIOSELECTIVE MICHAEL ADDITION; DOPAMINE BETA-HYDROXYLASE; TERMINAL ALKYNES; 1,3-DICARBONYL COMPOUNDS; CARBONYL GROUPS; ATOM ECONOMY; KETONES; 1,4-ADDITION; NITROOLEFINS; ALDEHYDES;
D O I
10.1039/c0cc02181d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric addition of (triisopropylsilyl)acetylene to nitroalkenes took place in the presence of a rhodium/chiral bisphosphine catalyst to give beta-alkynylated nitroalkanes in high yields with high enantioselectivity.
引用
收藏
页码:6837 / 6839
页数:3
相关论文
共 57 条
[1]   Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].
Alexakis, A ;
Benhaim, C ;
Rosse, S ;
Humam, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263
[2]   Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].
Andrey, O ;
Alexakis, A ;
Bernardinelli, G .
ORGANIC LETTERS, 2003, 5 (14) :2559-2561
[3]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[4]   Asymmetric catalysis .103. Enantioselective Michael addition of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].
Brunner, H ;
Kimel, B .
MONATSHEFTE FUR CHEMIE, 1996, 127 (10) :1063-1072
[5]   Catalytic and highly efficient 1,4-addition of terminal alkynes to conjugated enones by [RuCl2(p-cymene)]2/pyrrolidine [J].
Chang, S ;
Na, Y ;
Choi, E ;
Kim, S .
ORGANIC LETTERS, 2001, 3 (13) :2089-2091
[6]   The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones [J].
Chen, L ;
Li, CJ .
CHEMICAL COMMUNICATIONS, 2004, (20) :2362-2364
[7]   Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes [J].
Choi, H ;
Hua, ZH ;
Ojima, I .
ORGANIC LETTERS, 2004, 6 (16) :2689-2691
[8]   Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-nitroalkenes [J].
Cote, Alexandre ;
Lindsay, Vincent N. G. ;
Charette, Andre B. .
ORGANIC LETTERS, 2007, 9 (01) :85-87
[9]   Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond [J].
Cozzi, PG ;
Hilgraf, R ;
Zimmermann, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4095-4105
[10]   Rhodium-catalyzed enantioselective desymmetrization of bicyclic hydrazines with alkynylboronic esters [J].
Crotti, Stefano ;
Bertolini, Ferruccio ;
Macchia, Franco ;
Pineschi, Mauro .
CHEMICAL COMMUNICATIONS, 2008, (27) :3127-3129