cis-vinylphosphonates and 1,3-butadienylphosphonates by zirconation of 1-alkynylphosphonates

被引:48
作者
Quntar, AA [1 ]
Srebnik, M [1 ]
机构
[1] Hebrew Univ Jerusalem, Sch Pharm, Dept Med Chem & Nat Prod, IL-91120 Jerusalem, Israel
关键词
D O I
10.1021/ol0157454
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Addition of "zirconocene" to 1-alkynylphosphonates gives three-membered zirconacylces that can be hydrolyzed to cis-vinylphosphonates or further reacted with alkynes/hydrolysis to give substituted (Z,E)- and (E,E)-1,3-butadienylphosphonates.
引用
收藏
页码:1379 / 1381
页数:3
相关论文
共 39 条
[1]   THE SYNTHESIS OF DIETHYL PARA-TOLYLSULPHONYLETHYNYLPHOSPHONATE AND RELATED ACETYLENES, AND THEIR REACTIONS WITH NUCLEOPHILES, PYRIDINIUM-1-DICYANOMETHYLIDES, AND DIENES [J].
ACHESON, RM ;
ANSELL, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (06) :1275-1281
[2]   Acceleration of nucleophilic addition to vinylphosphonates and vinyl phosphine oxides by chlorotrimethylsilane [J].
Afarinkia, K ;
Binch, HM ;
Modi, C .
TETRAHEDRON LETTERS, 1998, 39 (40) :7419-7422
[3]  
BLACKBURN GM, 1979, J CHEM SOC P1, V44, P865
[4]   Stereoselective addition of sodium organyl chalcogenolates to alkynylphosphonates: synthesis of diethyl 2-(organyl)-2-(organochalcogenyl)vinylphosphonates [J].
Braga, AL ;
Alves, EF ;
Silveira, CC ;
de Andrade, LH .
TETRAHEDRON LETTERS, 2000, 41 (02) :161-163
[5]  
Brunner H, 2000, SYNLETT, P201
[6]  
CHANCE LH, 1975, Patent No. 3910886
[7]   A CONVENIENT STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED ALK-1-ENYL PHOSPHONATES [J].
CRISTAU, HJ ;
GASC, MB ;
MBIANDA, XY .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 474 (1-2) :C14-C15
[8]   Facile and stereoselective synthesis of vinylphosphonates [J].
Cristau, HJ ;
Mbianda, XY ;
Beziat, Y ;
Gasc, MB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :301-311
[9]   Dioxirane oxidation of substituted vinylphosphonates: a novel efficient route to 1,2-epoxyalkylphosphonates [J].
Cristau, HJ ;
Mbianda, XY ;
Geze, A ;
Beziat, Y ;
Gasc, MB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 571 (02) :189-193
[10]   One-pot synthesis of 1-alkynylphosphonates [J].
Gil, JM ;
Sung, JW ;
Park, CP ;
Oh, DY .
SYNTHETIC COMMUNICATIONS, 1997, 27 (18) :3171-3174