Enantioselective ene reaction of cyclopentadiene and α,β-enals catalyzed by a diphenylprolinol silyl ether

被引:92
作者
Gotoh, Hiroaki [1 ]
Masui, Ryouhei [1 ]
Ogino, Hiroshi [1 ]
Shoji, Mitsuru [1 ]
Hayashi, Yujiro [1 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
asymmetric synthesis; cyclopentadiene; Diels-Alder reaction; ene reaction; organocatalysis;
D O I
10.1002/anie.200602925
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The opposite result: A diphenylprolinol silyl ether promotes an intermolecular enantioselective ene reaction of α,β-enals with cyclopentadiene. This is the first example of cyclopentadiene acting as the ene component, and not the diene, with α,β-enals. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6853 / 6856
页数:4
相关论文
共 49 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]  
Berkssel A., 2005, ASYMMETRIC ORGANOCAT
[3]   CATALYTIC ASYMMETRIC CARBONYL-ENE REACTIONS [J].
BERRISFORD, DJ ;
BOLM, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16) :1717-1719
[4]  
BERRISFORD DJ, 1995, ANGEW CHEM, V107, P1862
[5]  
Brandau S., 2006, ANGEW CHEM, V118, P4411
[6]   Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].
Brandau, Sven ;
Landa, Aitor ;
Franzen, Johan ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309
[7]   Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones [J].
Chi, YG ;
Gellman, SH .
ORGANIC LETTERS, 2005, 7 (19) :4253-4256
[8]   Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids [J].
Chi, Yonggui ;
Gellman, Samuel H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6804-6805
[9]  
Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[10]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175