RADICAL CYCLIZATIONS OF N-VINYLIC ALPHA-CHLOROACETAMIDES - 5-ENDO-TRIG AND 4-EXO-TRIG CYCLIZATIONS

被引:98
作者
ISHIBASHI, H
NAKAMURA, N
SATO, T
TAKEUCHI, M
IKEDA, M
机构
[1] Kyoto Pharmaceutical University, Kyoto, 607, Misasagi, Yamashina
关键词
D O I
10.1016/S0040-4039(00)74314-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bu3SnH mediated radical cyclizations of N-vinylic alpha-chloroacetamides proceeded in a "disfavored" 5-endo-trig manner to give five-membered lactams. Some exceptions where the 4-exo cyclization predominates are also described.
引用
收藏
页码:1725 / 1728
页数:4
相关论文
共 36 条
[1]   STEREOSELECTIVE RADICAL CYCLIZATION FOR THE SYNTHESIS OF BICYCLIC HIGHER-CARBON SUGARS - SYNTHESIS OF THE SUGAR MOIETY OF OCTOSYL ACIDS [J].
ARAKI, Y ;
ENDO, T ;
ARAI, Y ;
TANJI, M ;
ISHIDO, Y .
TETRAHEDRON LETTERS, 1989, 30 (21) :2829-2832
[2]   5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].
BALDWIN, JE ;
CUTTING, J ;
DUPONT, W ;
KRUSE, L ;
SILBERMAN, L ;
THOMAS, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738
[3]   COBALT-MEDIATED CYCLIZATION OF AMINO-ACID DERIVATIVES - APPLICATION TO THE KAINOIDS [J].
BALDWIN, JE ;
LI, CS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :166-168
[4]   FORMATION OF FUSED BI-CYCLIC AND TRI-CYCLIC BETA-LACTAMS BY RADICAL RING-CLOSURE [J].
BECKWITH, ALJ ;
BOATE, DR .
TETRAHEDRON LETTERS, 1985, 26 (14) :1761-1764
[5]   PYRROLIZIDINONE AND INDOLIZIDINONE SYNTHESIS - GENERATION AND INTRAMOLECULAR ADDITION OF ALPHA-ACYLAMINO RADICALS TO OLEFINS AND ALLENES [J].
BURNETT, DA ;
CHOI, JK ;
HART, DJ ;
TSAI, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8201-8209
[6]   USEFUL CHEMISTRY OF 3-(1-METHYLETHYLIDENE)-4-ACETOXY-2-AZETIDINONE - A FORMAL SYNTHESIS OF (+/-)-ASPARENOMYCIN-C [J].
BUYNAK, JD ;
RAO, MN ;
PAJOUHESH, H ;
CHANDRASEKARAN, RY ;
FINN, K ;
DEMEESTER, P ;
CHU, SC .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4245-4252
[7]   THE USE OF ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE IN A SIMPLE SYNTHESIS OF PYRROLIDINES AND TETRAHYDROFURANS [J].
CASTAGNINO, E ;
CORSANO, S ;
BARTON, DHR .
TETRAHEDRON LETTERS, 1989, 30 (22) :2983-2986
[8]   REGIOSELECTIVITY IN THE RING-OPENING OF 2-METHYLCYCLOPROPYLCARBINYL AND 2-METHYLCYCLOBUTYLCARBINYL RADICALS [J].
CASTAING, M ;
PEREYRE, M ;
RATIER, M ;
BLUM, PM ;
DAVIES, AG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (03) :287-292
[9]  
CEKOVIC Z, 1972, TETRAHEDRON LETT, P749
[10]  
CLIVE DLJ, 1989, HETEROCYCLES, V28, P1157