Cyclisation of dienes using phosphorus-centred radicals to form organophosphorus adducts

被引:65
作者
Jessop, CM
Parsons, AF [1 ]
Routledge, A
Irvine, D
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] Uniqema, Middlesbrough TS90 9JE, Cleveland, England
基金
英国生物技术与生命科学研究理事会;
关键词
cyclisation; dienes; phosphorus compounds; radicals and radical reactions;
D O I
10.1016/S0040-4039(02)02610-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of various dienes with phosphites or related phosphorus hydrides, under free radical cyclisation conditions, affords cyclic organophosphorus adducts. This quick, mild and technically clean approach affords 5- and 6-ring carbocycles and heterocycles in good to excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:479 / 483
页数:5
相关论文
共 42 条
[21]   The synthesis of 4,5-methano congeners of alpha-kainic and alpha-allo-kainic acids as probes for glutamate receptors [J].
Hanessian, S ;
Ninkovic, S ;
Reinhold, U .
TETRAHEDRON LETTERS, 1996, 37 (50) :8971-8974
[22]   The stereocontrolled synthesis of enantiopure alpha-methano heterocycles and constrained amino acid analogs [J].
Hanessian, S ;
Reinhold, U ;
Ninkovic, S .
TETRAHEDRON LETTERS, 1996, 37 (50) :8967-8970
[23]   Free radical chain reactions for the preparation of novel anomeric carbohydrate difluoromethylene-phosphonates and -phosphonothioates. [J].
Herpin, TF ;
Motherwell, WB ;
Roberts, BP ;
Roland, S ;
Weibel, JM .
TETRAHEDRON, 1997, 53 (44) :15085-15100
[24]   Generation of aminoacyl radicals from 1-carbamoyl-1-methylcyclohexa-2,5-dienes:: a new tin-free homolytic route to β- and γ-lactams [J].
Jackson, LV ;
Walton, JC .
CHEMICAL COMMUNICATIONS, 2000, (23) :2327-2328
[25]   REACTION OF TERPENES WITH DIETHYL PHOSPHONATE UNDER FREE-RADICAL CONDITIONS [J].
KENNEY, RL ;
FISHER, GS .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (05) :682-686
[26]   A novel and efficient methodology for the C-C bond forming radical cyclization of hydrophobic substrates in water [J].
Kita, Y ;
Nambu, H ;
Ramesh, NG ;
Anilkumar, G ;
Matsugi, M .
ORGANIC LETTERS, 2001, 3 (08) :1157-1160
[27]   Generation of dialkyl phosphonodithioyl radicals and their addition onto alkenes. Synthesis of 3-phosphonodithiomethyl-3-deoxofuranosides [J].
Lopin, C ;
Gautier, A ;
Gouhier, G ;
Piettre, SR .
TETRAHEDRON LETTERS, 2000, 41 (52) :10195-10200
[28]  
Martin CG, 2000, TETRAHEDRON LETT, V41, P1833
[29]   Organic syntheses through free-radical annulations and related cascade sequences [J].
McCarroll, AJ ;
Walton, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (24) :3215-3229
[30]  
Nifantev E. E., 1991, J GEN CHEM USSR, V61, P83