STEREOCHEMISTRY OF THE P-C BOND FORMATION IN AN OXAZAPHOSPHOLIDINE BORANE COMPLEX

被引:94
作者
JUGE, S
STEPHAN, M
MERDES, R
GENET, JP
HALUTDESPORTES, S
机构
[1] ENSCP,SYNTH ORGAN LAB,URA 1381,F-75231 PARIS,FRANCE
[2] UNIV P & M CURIE,CHIM MET TRANSIT LAB,URA 419,F-75252 PARIS,FRANCE
关键词
D O I
10.1039/c39930000531
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of the 3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane complex 1 with organometallic reagents involves a stereoselective P-O bond cleavage; the X-ray structures of the starting complex 1 and of the aminophosphine boranes 2a, b, reveal a stereochemistry of the P-C bond formation with a retention of the configuration which is explained by a nucleophilic attack on the less hindered side-face of the pyramidal phosphorus atom.
引用
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页码:531 / 533
页数:3
相关论文
共 15 条
[1]   THE NUCLEOPHILIC DISPLACEMENT ROUTE TO HOMOCHIRAL ARYLPHOSPHINE OXIDES [J].
BROWN, JM ;
CAREY, JV ;
RUSSELL, MJH .
TETRAHEDRON, 1990, 46 (13-14) :4877-4886
[2]  
BRUNNER H, 1988, TOP STEREOCHEM, V18, P129
[3]   ASYMMETRIC TETRACOORDINATE PENTACOVALENT ORGANOPHOSPHORUS COMPOUNDS - THEIR RESOLUTION AND DETERMINATION OF ENANTIOMERIC PURITY [J].
HALL, CR ;
INCH, TD .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1979, 7 (02) :171-184
[4]  
HALL CR, 1979, TETRAHEDRON LETT, V29, P2729
[5]   SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES [J].
IMAMOTO, T ;
OSHIKI, T ;
ONOZAWA, T ;
KUSUMOTO, T ;
SATO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5244-5252
[6]   EFFICIENT ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE TERTIARY MONO AND DIPHOSPHINE LIGANDS [J].
JUGE, S ;
STEPHAN, M ;
LAFFITTE, JA ;
GENET, JP .
TETRAHEDRON LETTERS, 1990, 31 (44) :6357-6360
[7]   STRUCTURES OF (2R,4S,5R)-3,4-DIMETHYL-2,5-DIPHENYL-1,3,2-OXAZAPHOSPHOLIDINE(P-B)BORANE (1) AND OF (2R,5S)-5-METHYL-2,4,4-TRIPHENYL-1,3,2-DIOXAPHOSPHOLANE(P-B)BORANE (2) [J].
JUGE, S ;
STEPHAN, M ;
GENET, JP ;
HALUTDESPORTES, S ;
JEANNIN, S .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1990, 46 :1869-1872
[8]  
Juge S., 1991, Intern. Patent, Patent No. [5043465, US5043465]
[9]  
Kagan H.B., 1990, CHEM ORGANOPHOSPHORU, V1, P51
[10]   GRIGNARD REACTION OF 2-PHENYL-TETRAHYDROPYRROLO-1,3,2-OXAZAPHOSPHOLES, OBSERVATION OF THE STEREOSPECIFIC INVERSION OF CONFIGURATION [J].
KOIZUMI, T ;
YANADA, R ;
TAKAGI, H ;
HIRAI, H ;
YOSHII, E .
TETRAHEDRON LETTERS, 1981, 22 (06) :571-572