Ceric ammonium nitrate promoted free radical cyclization reactions leading to beta-lactams

被引:23
作者
DAnnibale, A
Pesce, A
Resta, S
Trogolo, C
机构
[1] Ctr. C.N.R. di Stud. per la C., Dipartimento di Chimica, Università La Sapienza, 00185 Roma
关键词
D O I
10.1016/S0040-4039(97)00162-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of enamides with CAN in methanol affords variously functionalized beta-lactams through a 4-exo-trig cyclization of alpha-carbamoylalkyl radicals in most cases products with trans stereochemistry on be obtained. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1829 / 1832
页数:4
相关论文
共 21 条
[1]   SYNTHESIS OF 3-ACYL AND 3-CARBOALKOXYFURANS BY THE CERIC AMMONIUM-NITRATE PROMOTED ADDITION OF 1,3-DICARBONYL COMPOUNDS TO VINYLIC ACETATES [J].
BACIOCCHI, E ;
RUZZICONI, R .
SYNTHETIC COMMUNICATIONS, 1988, 18 (15) :1841-1846
[2]   RELATIVE RATES FOR THE ADDITION-REACTIONS OF THE MALONYL RADICAL TO SUBSTITUTED STYRENES INDUCED BY CERIUM(IV) AMMONIUM-NITRATE AND TRIBUTYLTIN HYDRIDE - A COMPARISON [J].
BACIOCCHI, E ;
GIESE, B ;
FARSHCHI, H ;
RUZZICONI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5688-5691
[3]   CERIUM(IV) AMMONIUM-NITRATE PROMOTED OXIDATIVE CYCLIZATION OF DIMETHYL 4-PENTENYLMALONATE [J].
BACIOCCHI, E ;
PAOLOBELLI, AB ;
RUZZICONI, R .
TETRAHEDRON, 1992, 48 (22) :4617-4622
[4]   ELECTRONIC AND STERIC EFFECTS IN THE ADDITION OF ELECTROPHILIC 1,3-DICARBONYLALKYL RADICALS TO STYRENES [J].
BACIOCCHI, E ;
RUZZICONI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4772-4778
[5]  
BACIOCCHI E, 1989, NATO ADV SCI I C-MAT, V260, P155
[6]   MN(III) - PROMOTED CYCLIZATION OF ENAMIDES - AN OXIDATIVE RADICAL APPROACH TO BETA-LACTAMS [J].
DANNIBALE, A ;
RESTA, S ;
TROGOLO, C .
TETRAHEDRON LETTERS, 1995, 36 (49) :9039-9042
[7]   Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides. [J].
DAnnibale, A ;
Pesce, A ;
Resta, S ;
Trogolo, C .
TETRAHEDRON LETTERS, 1996, 37 (41) :7429-7432
[8]  
FREEMONT SL, 1991, TETRAHEDRON LETT, V32, P2335
[9]   COBALT-MEDIATED REACTIONS - A NEW SYNTHETIC APPROACH TO BETA-LACTAM, GAMMA-LACTAM AND DELTA-LACTAM [J].
GILL, GB ;
PATTENDEN, G ;
REYNOLDS, SJ .
TETRAHEDRON LETTERS, 1989, 30 (24) :3229-3232
[10]  
ISHIBASHI H, 1993, SYNLETT, P649