trans-cis-Isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines on heating with triallylborane. Synthesis of (+/-)-dihydropinidine.

被引:22
作者
Bubnov, YN [1 ]
Klimkina, EV [1 ]
Ignatenko, AV [1 ]
Gridnev, ID [1 ]
机构
[1] RUSSIAN ACAD SCI,AN NESMEYANOV ORGANOELEMENT CPDS INST,MOSCOW,RUSSIA
关键词
D O I
10.1016/S0040-4039(97)00953-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method for isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines into the corresponding cis-isomers is presented. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4631 / 4634
页数:4
相关论文
共 18 条
[1]   DEFENSE-MECHANISMS OF ANTHROPODS .119. ALKALOIDS OF THE MEXICAN BEAN BEETLE, EPILACHNA-VARIVESTIS (COCCINELLIDAE) [J].
ATTYGALLE, AB ;
XU, SC ;
MCCORMICK, KD ;
MEINWALD, J ;
BLANKESPOOR, CL ;
EISNER, T .
TETRAHEDRON, 1993, 49 (41) :9333-9342
[2]   THE DEFENSIVE ALKALOIDS OF CRYPTOLAEMUS-MONTROUZIERI (COLEOPTERA, COCCINELLIDAE) [J].
BROWN, WV ;
MOORE, BP .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (06) :1255-1261
[3]   Preparation of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines by reductive trans-2,6-dialkylation of pyridine. Synthesis of (+/-)-epidihydropinidine [J].
Bubnov, YN ;
Klimkina, EV ;
Ignatenko, AV ;
Gridnev, ID .
TETRAHEDRON LETTERS, 1996, 37 (08) :1317-1320
[4]   REDUCTIVE MONO-ALPHA AND TRANS-ALPHA, ALPHA'-DIALLYLATION OF AROMATIC NITROGEN-HETEROCYCLES BY ALLYLBORANES [J].
BUBNOV, YN .
PURE AND APPLIED CHEMISTRY, 1994, 66 (02) :235-244
[5]  
BUBNOV YN, 1994, IZV AKAD NAUK SER K, V43, P693
[6]  
BUBNOV YN, 1994, IZV AKAD NAUK SER K, V43, P705
[7]   Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D [J].
Chenevert, R ;
Dickman, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3332-3341
[8]   STEREOCONTROLLED PREPARATION OF CIS-2,6-DIALKYLPIPERIDINE AND TRANS-2,6-DIALKYLPIPERIDINE VIA 1-ACYLDIHYDROPYRIDINE INTERMEDIATES - SYNTHESIS OF (+/-)-SOLENOPSIN-A AND (+/-)-DIHYDROPINIDINE [J].
COMINS, DL ;
WEGLARZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2506-2512
[9]  
COMINS DL, 1994, HETEROCYCLES, V37, P1121
[10]   ENANTIOSELECTIVE SYNTHESIS OF (+)-PINIDINE [J].
DOLLE, RE ;
OSIFO, KI ;
LI, CS .
TETRAHEDRON LETTERS, 1991, 32 (38) :5029-5030