Pd0-catalyzed three-component tandem double-addition-cyclization reaction:: Stereoselective synthesis of cis-pyrrolidine derivatives

被引:47
作者
Ma, SM [1 ]
Jiao, N [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1002/anie.200290033
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cis-2,5-Disubstituted pyrrolidine skeletons have been constructed by the Pd0- catalyzed three-component tandem double-addition-cyclization reaction of 2-(2,3-butadienyl)malonates, organohalides, and imines (see scheme, yields: 81-100%; cis/trans > 95:5).
引用
收藏
页码:4737 / 4740
页数:4
相关论文
共 49 条
[1]   SYNTHESIS OF 1,3-DIENES AND FUNCTIONALIZED STYRENES BY CATALYTIC CARBOPALLADATION OF ALLENES [J].
AHMAR, M ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1984, 25 (40) :4505-4508
[2]   CARBOPALLADATION OF BETA-ALLENYLMALONATES - A WAY TO CYCLOPENTENYL OR VINYLCYCLOPROPYL DERIVATIVES [J].
AHMAR, M ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1985, 26 (32) :3795-3798
[3]   Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].
Arredondo, VM ;
Tian, S ;
McDonald, FE ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639
[4]  
BACKVALL JE, 1990, J ORG CHEM, V55, P826, DOI 10.1021/jo00290a010
[5]   PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 2,3-BUTADIANYLMALONATES TO GAMMA-LACTONES [J].
BESSON, L ;
BAZIN, J ;
GORE, J ;
CAZES, B .
TETRAHEDRON LETTERS, 1994, 35 (18) :2881-2884
[6]   Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-β-iodination of amino acids [J].
Boto, A ;
Hernández, R ;
de León, Y ;
Suárez, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7796-7803
[7]   RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].
BUNCE, RA .
TETRAHEDRON, 1995, 51 (48) :13103-13159
[8]   ASYMMETRIC-SYNTHESIS OF FUNCTIONALIZED PYRROLIDINES - HIGHLY DIASTEREOSELECTIVE CYCLIZATIONS MEDIATED BY SULFIDE AND SULFOXIDE LIGANDS [J].
DAVIES, IW ;
GALLAGHER, T ;
LAMONT, RB ;
SCOPES, DIC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :335-337
[9]  
DAVIES IW, 1993, SYNLETT, P85
[10]  
Delaude, 1986, ALKALOIDS, V27, P269