Regio- and Stereoselective Isomerizations of Allenamides: Synthesis of 2-Amido-Dienes and Their Tandem Isomerization-Electrocyclic Ring-Closure

被引:56
作者
Hayashi, Ryuji
Hsung, Richard P. [1 ]
Feltenberger, John B.
Lohse, Andrew G.
机构
[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
关键词
DIELS-ALDER REACTIONS; STEREOCHEMICAL ASSIGNMENT; COPPER; ESTERS; 2-AMINO-1,3-BUTADIENES; 1,3,5-HEXATRIENES; AMIDATION; CATALYSTS; HALIDES; DIENES;
D O I
10.1021/ol900647s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regio- and stereoselective isomerization of allenamides is described, leading to preparations of de novo 2-amido-dienes and a tandem isomerization-6 pi-electron electrocyclic ring-closure.
引用
收藏
页码:2125 / 2128
页数:4
相关论文
共 59 条
[1]   Palladium-catalyzed hydrocarboxylation of allenes [J].
Al-Masum, M ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3809-3810
[2]   A SIMPLE AND EFFICIENT SYNTHESIS OF 2-AMINO-1,3-BUTADIENES FROM BETA-ENAMINO PHOSPHONIUM SALTS [J].
BARLUENGA, J ;
MERINO, I ;
PALACIOS, F .
TETRAHEDRON LETTERS, 1990, 31 (46) :6713-6716
[3]   Cyclic BF2 adducts of functionalized fischer vinylcarbene complexes:: Preparation and stereoselective Diels-Alder reactions with 2-amino 1,3-dienes [J].
Barluenga, J ;
Canteli, RM ;
Florez, J ;
Garcia-Granda, S ;
Gutierrez-Rodriguez, A ;
Martin, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2514-2522
[4]   Retro-ene reactions in acylallene derivatives [J].
Bibas, H ;
Koch, R ;
Wentrup, C .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2619-2626
[5]   DIMETHYLENECYCLOPROPANE [J].
BLOCH, R ;
LEPERCHE.P ;
CONIA, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (10) :798-&
[6]   Gold(I)-catalyzed isomerization of allenyl carbinol esters: An efficient access to functionalized 1,3-butadien-2-ol esters [J].
Buzas, Andrea K. ;
Istrate, Florin M. ;
Gagosz, Fabien .
ORGANIC LETTERS, 2007, 9 (06) :985-988
[7]  
CAMPBELL AL, 1987, SYNTHESIS-STUTTGART, P421
[8]   PYROLYSIS OF ALKENYLIDENECYCLOPROPANES . A CONVENIENT SYNTHESIS OF DIMETHYLENECYCLOPROPANES [J].
CRANDALL, JK ;
PAULSON, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (18) :4302-&
[9]   Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].
Dehli, JR ;
Legros, J ;
Bolm, C .
CHEMICAL COMMUNICATIONS, 2005, (08) :973-986
[10]   Secondary orbital effect in the electrocyclic ring closure of 7-azahepta-1,2,4,6-tetraene - A CASSCF molecular orbital study [J].
Duncan, James A. ;
Calkins, David E. G. ;
Chavarha, Mariya .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6740-6748