5-Endo-trig radical cyclizations

被引:113
作者
Ishibashi, H [1 ]
Sato, T
Ikeda, M
机构
[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan
[2] Kyoto Pharmaceut Univ, Yamashina, Kyoto 6078414, Japan
来源
SYNTHESIS-STUTTGART | 2002年 / 06期
关键词
alkaloids; tributyltin hydride; cyclizations; 5-endo-trig; alpha-halo amides; manganese(III) acetate; radicals;
D O I
10.1055/s-2002-25759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Endo-trig ring-closure is recognized as a disfavored process. However, a number of examples of such a type of cyclization have recently been reported. This review focuses on studies of 5-endo-trig radical cyclizations that provide new syntheses of five-membered carbo- and heterocyclic compounds.
引用
收藏
页码:695 / 713
页数:19
相关论文
共 114 条
[1]  
Baker SR, 1998, TETRAHEDRON LETT, V39, P7197
[2]   Tandem radical cyclisation of enamides mediated by tin hydride; pyrrolizidinone or indolizidinone ring formation [J].
Baker, SR ;
Burton, KI ;
Parsons, AF ;
Pons, JF ;
Wilson, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04) :427-436
[3]  
Baker SR, 1998, TETRAHEDRON LETT, V39, P2815
[4]   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
[5]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[6]   REGIOCHEMISTRY OF ALKENYLSILYL AND ALKENYLDISILANYL RADICAL CYCLIZATIONS [J].
BARTON, TJ ;
REVIS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) :3802-3805
[7]   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
[8]   FREE-RADICAL CYCLIZATIONS LEADING TO NITROGEN-HETEROCYCLES .2. 2-PHENYLPYRAZOLIDIN-3-ONES VIA TRIBUTYLTIN HYDRIDE REACTION WITH ALPHA-BROMOACYLATED PHENYLHYDRAZONES [J].
BELLETIRE, JL ;
HAGEDORN, CE ;
HO, DM ;
KRAUSE, J .
TETRAHEDRON LETTERS, 1993, 34 (05) :797-800
[9]   5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers.: A highly diastereoselective access to functionalized cyclopentanes [J].
Bogen, S ;
Gulea, M ;
Fensterbank, L ;
Malacria, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4920-4925
[10]   5-endo-trig Radical cyclizations: A new means to the stereoselective synthesis of cyclopentanes and diquinanes [J].
Bogen, S ;
Malacria, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) :3992-3993