Radical addition reactions of chiral phosphorus hydrides

被引:26
作者
Jessop, CM
Parsons, AF [1 ]
Routledge, A
Irvine, DJ
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] Uniqema, Wilton Ctr, Redcar TS10 4RF, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1016/j.tetasy.2003.04.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2849 / 2851
页数:3
相关论文
共 22 条
[1]  
Afarinkia K, 2003, SYNLETT, P509, DOI 10.1055/s-2003-37510
[2]   Triethylborane-initiated room temperature radical addition of hypophosphites to olefins:: Synthesis of monosubstituted phosphinic acids and esters [J].
Deprèle, S ;
Montchamp, JL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6745-6755
[3]   Efficient synthesis of 3-furanosyl-6′-furanosylphosphinate through a tandem sequential radical process [J].
Dubert, O ;
Gautier, A ;
Condamine, E ;
Piettre, SR .
ORGANIC LETTERS, 2002, 4 (03) :359-362
[4]  
FARNHAM WB, 1971, CHEM COMMUN, P146
[5]   Efficient and practical aerobic radical addition of thiophosphites to alkenes [J].
Gautier, A ;
Garipova, G ;
Dubert, O ;
Oulyadi, H ;
Piettre, SR .
TETRAHEDRON LETTERS, 2001, 42 (33) :5673-5676
[6]  
GULEAPURCARESCU M, 1995, TETRAHEDRON LETT, V36, P6635
[7]   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
[9]   Cyclisation of dienes using phosphorus-centred radicals to form organophosphorus adducts [J].
Jessop, CM ;
Parsons, AF ;
Routledge, A ;
Irvine, D .
TETRAHEDRON LETTERS, 2003, 44 (03) :479-483
[10]   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