1,4-pentadienyl-3-sulfonamides: Frameworks for "disfavored" radical cascade cyclizations

被引:22
作者
Bommezijn, S [1 ]
Martin, CG [1 ]
Kennedy, AR [1 ]
Lizos, D [1 ]
Murphy, JA [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
关键词
D O I
10.1021/ol0166449
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 1,4-Pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.
引用
收藏
页码:3405 / 3407
页数:3
相关论文
共 26 条
[1]   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
[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]   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
[4]   FREE-RADICAL ADDITION OF ISOBUTYRIC ACID TO ALPHA, OMEGA-DIOLEFINS - NEW ROUTE TO ALPHA, ALPHA, ALPHA', ALPHA'-TETRAMETHYLALKANEDIOIC ACIDS [J].
BRADNEY, MAM ;
FORBES, AD ;
WOOD, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (12) :1655-1660
[5]   Radical sequential processes promoted by 1,5-radical translocation reaction: Formation and [3+2] anulation of alkenesulfanyl radicals [J].
Capella, L ;
Montevecchi, PC ;
Navacchia, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6783-6789
[6]  
Cassayre J, 2000, SYNLETT, P471
[7]  
Chatgilialoglu C, 1999, CHEM-EUR J, V5, P2866, DOI 10.1002/(SICI)1521-3765(19991001)5:10<2866::AID-CHEM2866>3.0.CO
[8]  
2-6
[9]   MECHANISM OF THE REARRANGEMENT OF 2(VINYLOXY)ALKYL TO 4-KETOBUTYL RADICALS [J].
CRICH, D ;
YAO, QW .
TETRAHEDRON, 1994, 50 (43) :12305-12312
[10]   A NEW C-C BOND-FORMING FREE-RADICAL REARRANGEMENT [J].
CRICH, D ;
YAO, QW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) :1265-1267