Synthesis of substituted P-stereogenic vinylphosphine oxides by olefin cross-metathesis

被引:53
作者
Demchuk, OM
Pietrusiewicz, KM
Michrowska, A
Grela, K
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
[2] Marie Curie Sklodowska Univ, Dept Organ Chem, PL-20614 Lublin, Poland
关键词
D O I
10.1021/ol035011m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Substituted vinylphosphine oxides have been prepared in good yield and exclusive (E)-olefin selectivity via olefin cross-metathesis using Grubbs and Hoveyda-type ruthenium catalysts. In addition, metathesis of chiral vinylphosphine oxides proceeds without racemization of the phosphorus chirality center, providing easy access to functionalized chiral nonracemic (E)-alkenylphosphine oxides.
引用
收藏
页码:3217 / 3220
页数:4
相关论文
共 45 条
[1]   A NEW P-CHIRAL AMINOPHOSPHINE LIGAND CONTAINING A 2,2'-COUPLED PYRROLIDINE-PHOSPHOLANE RING-SYSTEM - SYNTHESIS AND COORDINATION PROPERTIES WITH RHODIUM(I) AND IRIDIUM(I) FRAGMENTS [J].
BIANCHINI, C ;
CICCHI, S ;
PERUZZINI, M ;
PIETRUSIEWICZ, KM ;
BRANDI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) :833-834
[2]   RADICAL-ADDITION TO VINYLPHOSPHINE OXIDES - 1,2-STEREOINDUCTION OF PHOSPHORUS STEREOGENIC CENTER [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
PIETRUSIEWICZ, KM .
TETRAHEDRON LETTERS, 1991, 32 (27) :3265-3268
[3]   CHIRAL VINYL PHOSPHINE OXIDES - DOUBLE ASYMMETRIC INDUCTION IN THE 1,3-DIPOLAR CYCLOADDITION TO CHIRAL NITRONES - KINETIC RESOLUTION OF A RACEMIC PHOSPHOLENE OXIDE [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
PIETRUSIEWICZ, KM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4) :155-158
[4]   DIASTEREOFACIAL SELECTIVITY IN 1,3-DIPOLAR CYCLO-ADDITION TO METHYLPHENYLVINYLPHOSPHINE OXIDE [J].
BRANDI, A ;
CANNAVO, P ;
PIETRUSIEWICZ, KM ;
ZABLOCKA, M ;
WIECZOREK, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3073-3077
[5]   STEREOSELECTIVE NITRONE ADDITIONS TO VINYLPHOSPHINE DERIVATIVES - EFFECT OF PHOSPHORUS SUBSTITUENTS ON REACTION DIASTEREOSELECITIVITY [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
PIETRUSIEWICZ, KM ;
ZABLOCKA, M ;
WISNIEWSKI, W .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4383-4388
[6]   SINGLE AND DOUBLE ASYMMETRIC INDUCTION IN THE CYCLOADDITION OF CHIRAL NITRONES TO ACHIRAL AND CHIRAL VINYLPHOSPHINE OXIDES [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
PIETRUSIEWICZ, KM .
TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :1063-1074
[7]   A highly efficient and practical synthesis of cyclic phosphinates using ring-closing metathesis [J].
Bujard, M ;
Gouverneur, V ;
Mioskowski, C .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :2119-2123
[8]   A NOVEL DISPLACEMENT ROUTE TO P-CHIRAL PHOSPHINE OXIDES OF HIGH ENANTIOMERIC PURITY [J].
CARDELLICCHIO, C ;
FIANDANESE, V ;
NASO, F ;
PACIFICO, S ;
KOPROWSKI, M ;
PIETRUSIEWICZ, KM .
TETRAHEDRON LETTERS, 1994, 35 (34) :6343-6346
[9]   Synthesis of symmetrical trisubstituted olefins by cross metathesis [J].
Chatterjee, AK ;
Sanders, DP ;
Grubbs, RH .
ORGANIC LETTERS, 2002, 4 (11) :1939-1942
[10]  
Chatterjee AK, 2002, ADV SYNTH CATAL, V344, P634, DOI 10.1002/1615-4169(200208)344:6/7<634::AID-ADSC634>3.0.CO