THE FIRST [4+3] ANNULATION OF FISCHER CARBENE COMPLEXES WITH AZADIENES - FACILE SYNTHESIS OF AZEPINES

被引:30
作者
BARLUENGA, J
TOMAS, M
BALLESTEROS, A
SANTAMARIA, J
LOPEZORTIZ, F
机构
关键词
D O I
10.1039/c39940000321
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of 3-iminoprop-1-enylamines 1 with pentacarbonyl(1-methoxyprop-2-enylidene)chromium(O) complexes leads stereoselectively to substituted 5H-6,7-dihydroazepines in high yields; the process takes place at low temperature and is thought to involve a tandem imine cyclopropanation-Cope rearrangement.
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页码:321 / 322
页数:2
相关论文
共 12 条
[1]  
AUMANN R, 1993, SYNLETT, P669
[2]   AN EXPEDITIOUS STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED 7-MEMBERED CARBOCYCLES BY REACTION OF 2-AMINOBUTA-1,3-DIENES WITH VINYLCHROMIUM FISCHER TYPE CARBENES [J].
BARLUENGA, J ;
AZNAR, F ;
MARTIN, A ;
GARCIAGRANDA, S ;
SALVADO, MA ;
PERTIERRA, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) :319-321
[3]   2-AMINO-1,3-BUTADIENES AS CHIRAL BUILDING-BLOCKS - ENANTIOSELECTIVE SYNTHESIS OF 4-PIPERIDONES, 4-NITROCYCLOHEXANONES, AND 1,3-CYCLOHEPTADIONE DERIVATIVES [J].
BARLUENGA, J ;
AZNAR, F ;
VALDES, C ;
MARTIN, A ;
GARCIAGRANDA, S ;
MARTIN, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4403-4404
[4]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[5]   TANDEM CYCLOPROPANATION COPE REARRANGEMENT - A GENERAL-METHOD FOR THE CONSTRUCTION OF 7-MEMBERED RINGS [J].
DAVIES, HML .
TETRAHEDRON, 1993, 49 (24) :5203-5223
[6]   MEDIUM RING NITROGEN-HETEROCYCLES [J].
EVANS, PA ;
HOLMES, AB .
TETRAHEDRON, 1991, 47 (44) :9131-9166
[7]   TRANSITION-METAL CARBENE COMPLEXES .92. TRIPHENYLSILYLETHOXYCARBENEPENTACARBONYLCHROMIUM AND TRIPHENYLSILYLDIMETHYLAMINOCARBENEPENTACARBONYLCHROMIUM, 2 NEW CARBENE COMPLEXES [J].
FISCHER, EO ;
HOLLFELDER, H ;
KREISSL, FR ;
UEDELHOVEN, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 113 (03) :C31-C34
[8]   REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES - SYNTHESIS OF BETA-LACTAMS [J].
HEGEDUS, LS ;
MCGUIRE, MA ;
SCHULTZE, LM ;
YIJUN, C ;
ANDERSON, OP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) :2680-2687
[9]  
MURRAY CK, 1990, ORGANOMETALLICS, P3142
[10]  
SMALLEY RK, 1984, COMPREHENSIVE HETERO, P491