Palladium-catalyzed regio- and diastereoselective allylic alkylation with azlactones using triphenylarsine

被引:17
作者
Kawatsura, Motoi [1 ]
Ikeda, Daiji
Ishii, Tamiko
Komatsu, Yuji
Uenishi, Junichi
机构
[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan
[2] Kyoto Pharmaceut Univ, Kyoto 6078412, Japan
关键词
palladium catalysis; triphenylarsine; regioselectivity; diastereoselectivity; alkylations;
D O I
10.1055/s-2006-950400
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed regio- and diastereoselective allylic alkylation of (R)-2-acetoxy-4-phenyl-3-butene with azlactones using AsPh3 successfully occurred. The stereochemistries were highly controlled, and the reaction produced a coupling product which possessed vicinal chiral quaternary and tertiary carbon centers.
引用
收藏
页码:2435 / 2438
页数:4
相关论文
共 34 条
[1]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[2]  
2-V
[3]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[4]  
2-V
[5]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066
[6]   Catalytic asymmetric reactions via π-allylpalladium complexes coordinated with chiral monophosphine ligands [J].
Hayashi, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :195-202
[7]   Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].
Helmchen, G ;
Pfaltz, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345
[8]   Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions [J].
Ikeda, D ;
Kawatsura, M ;
Uenishi, J .
TETRAHEDRON LETTERS, 2005, 46 (39) :6663-6666
[9]   ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-ALPHA-ALKYLAMINO ACIDS BY ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES [J].
ITO, Y ;
SAWAMURA, M ;
SHIRAKAWA, E ;
HAYASHIZAKI, K ;
HAYASHI, T .
TETRAHEDRON, 1988, 44 (17) :5253-5262
[10]  
JOHNSON M, 1998, CHEM REV, P1689