ω-Ethylenic Allylic Substrates as Alternatives to Cyclic Substrates in Copper- and Iridium-Catalyzed Asymmetric Allylic Alkylation

被引:28
作者
Giacomina, Francesca [1 ]
Riat, David [1 ]
Alexakis, Alexandre [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
基金
新加坡国家研究基金会;
关键词
CONJUGATE ADDITION; LIGANDS; OLEFINS;
D O I
10.1021/ol100162y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy to access highly enantioenriched cyclic compounds (up to 98%) is proposed using omega-ethylenic allylic substrates through a one-pot asymmetric allylic alkylation and ring-closing metathesis. Such starting compounds can be seen as synthetic equivalents of cyclic allylic substrates.
引用
收藏
页码:1156 / 1159
页数:4
相关论文
共 26 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]   The copper-catalyzed asymmetric allylic substitution [J].
Alexakis, A ;
Malan, C ;
Lea, L ;
Tissot-Croset, K ;
Polet, D ;
Falciola, C .
CHIMIA, 2006, 60 (03) :124-130
[3]   Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones [J].
Alexakis, A ;
Albrow, V ;
Biswas, K ;
d'Augustin, M ;
Prieto, O ;
Woodward, S .
CHEMICAL COMMUNICATIONS, 2005, (22) :2843-2845
[4]   Tandem copper-catalyzed enantioselective allylation-metathesis [J].
Alexakis, A ;
Croset, K .
ORGANIC LETTERS, 2002, 4 (23) :4147-4149
[5]  
Alexakis A, 2001, SYNLETT, P1375
[6]  
Breit B, 2001, ADV SYNTH CATAL, V343, P429, DOI 10.1002/1615-4169(200107)343:5<429::AID-ADSC429>3.0.CO
[7]  
2-K
[8]  
CROSET K, 2004, ANGEW CHEM INT EDIT, V43, P2426
[9]   β- and γ-disubstituted olefins:: Substrates for copper-catalyzed asymmetric allylic substitution [J].
Falciola, Caroline A. ;
Tissot-Croset, Karine ;
Reyneri, Hugo ;
Alexakis, Alexandre .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) :1090-1100
[10]   Copper-catalyzed asymmetric allylic alkylation [J].
Falciola, Caroline A. ;
Alexakis, Alexandre .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (22) :3765-3780