β-alkyl-α-allylation of Michael acceptors through the palladium-catalyzed three-component coupling between allylic substrates, trialkylboranes, and activated olefins

被引:16
作者
Patil, NT [1 ]
Huo, ZB [1 ]
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/jo0524876
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The palladium-catalyzed three-component beta-alkyl-alpha-allylation reaction of activated olefins has been achieved. For example, in the presence of 5 mol % of Pd(PPh3)(4), the reaction of benzylidenemalononitrile 1a with Et3B and allyl acetate 2a in THF proceeded smoothly at 40 degrees C to give the corresponding beta-ethyl-alpha-allylated product 3a in 81% yield.
引用
收藏
页码:2503 / 2506
页数:4
相关论文
共 31 条
[1]   Palladium-catalyzed aminoallylation of activated olefins with allylic halides and phthalimide [J].
Aoyagi, K ;
Nakamura, H ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :5977-5980
[2]   A versatile palladium-mediated three-component reaction for the one-pot synthesis of stereodefined 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans [J].
Bottex, M ;
Cavicchioli, M ;
Hartmann, B ;
Monteiro, N ;
Balme, G .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :175-179
[3]   Three partners for a one pot palladium-mediated synthesis of various tetrahydrofurans. [J].
Cavicchioli, M ;
Sixdenier, E ;
Derrey, A ;
Bouyssi, D ;
Balme, G .
TETRAHEDRON LETTERS, 1997, 38 (10) :1763-1766
[4]   Triethylborane triggered intermolecular domino Michael-aldol three-component coupling reactions [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Reddy, NR ;
Reddy, MS .
TETRAHEDRON LETTERS, 2003, 44 (12) :2583-2585
[5]   A one pot synthesis of various Pyrrolidines via a tandem Michael addition-transition metal-catalysed cyclisation reaction. [J].
Clique, B ;
Monteiro, N ;
Balme, G .
TETRAHEDRON LETTERS, 1999, 40 (07) :1301-1304
[6]   Highly regio- and chemoselective palladium-catalyzed propargylallylation of activated olefins: A novel route to 1,7-enyne derivatives [J].
Jeganmohan, M ;
Shanmugasundaram, M ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4053-4062
[7]   Highly regio- and chemoselective palladium-catalyzed three-component assembly of arylethylidene malononitriles, allylic chlorides, and allenylstannanes: A novel route to 1,7-enyne derivatives [J].
Jeganmohan, M ;
Shanmugasundaram, M ;
Cheng, CH .
ORGANIC LETTERS, 2003, 5 (06) :881-884
[8]   Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction [J].
Kamijo, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11940-11945
[9]   Novel synthetic route to allyl cyanamides: Palladium-catalyzed coupling of isocyanides, allyl carbonate, and trimethylsilyl azide [J].
Kamijo, S ;
Jin, TN ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9453-9454
[10]  
Marat X, 1997, SYNLETT, P845