ATTEMPTED RESOLUTION OF FREE (+/-)-CHLOROPHENYLISOPROPYLPHOSPHINE

被引:37
作者
PABEL, M [1 ]
WILLIS, AC [1 ]
WILD, SB [1 ]
机构
[1] AUSTRALIAN NATL UNIV,INST ADV STUDIES,RES SCH CHEM,CANBERRA,ACT 0200,AUSTRALIA
关键词
D O I
10.1016/0957-4166(95)00314-F
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(+/-)-Chlorophenylisopropylphosphine has been resolved in a palladium(II) complex containing the phosphine and ortho-metalated (R)-1-[1-(dimethylamino)ethyl]naphthalene; the configurationally homogeneous (R,Rp) diastereomer of the complex crystallises from the reaction mixture by typical second-order asymmetric transformation in overall 82% yield. The absolute configuration of the complex was determined by X-ray crystallography. The pure (R,Rp) diastereomer of the complex reacts quantitatively with methanol in the presence of triethylamine to give the corresponding methoxyphosphine complex with complete stereoselectivity and inversion at phosphorus. All attempts at liberating optically active chlorophosphine from the palladium complex were unsuccessful.
引用
收藏
页码:2369 / 2374
页数:6
相关论文
共 23 条
[1]   NOVEL RING-OPENING AND HALOGEN TRANSFER FROM PLATINUM(II) TO PHOSPHORUS IN THE REACTION OF [PTCL2(CNR)2] (R = BU-T, P-MEOC6H4) WITH THE PHOSPHIRENE RING PPHCPH=CPH - CRYSTAL AND MOLECULAR-STRUCTURE OF THE DIMERIC CHLOROPHOSPHANE COMPLEX [PTCL(PCLPHCPH=CPH) (CNBU-T)]2 [J].
AJULU, FA ;
HITCHCOCK, PB ;
MATHEY, F ;
MICHELIN, RA ;
NIXON, JF ;
POMBEIRO, AJL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :142-143
[2]   CONTRASTING BEHAVIOR OF RELATED PALLADIUM COMPLEX-DERIVED RESOLVING AGENTS - 8-H CONFORMATIONAL LOCKING OF THE 1-NAPHTHYL SIDE-CHAIN [J].
ALCOCK, NW ;
HULMES, DI ;
BROWN, JM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) :395-397
[3]   RESOLUTIONS INVOLVING METAL COMPLEXATION - PREPARATION AND RESOLUTION OF (R,S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE AND ITS ARSENIC ANALOG - CRYSTAL AND MOLECULAR-STRUCTURE OF (+)589-[(R)-DIMETHYL(1-ETHYL-ALPHA-NAPHTHYL)AMINATO-C-2, N][(S)-METHYLPHENYL(8-QUINOLYL)PHOSPHINE]PALLADIUM(II) HEXAFLUOROPHOSPHATEOG [J].
ALLEN, DG ;
MCLAUGHLIN, GM ;
ROBERTSON, GB ;
STEFFEN, WL ;
SALEM, G ;
WILD, SB .
INORGANIC CHEMISTRY, 1982, 21 (03) :1007-1014
[4]  
BAECHLER RD, 1971, J AM CHEM SOC, V93, P773
[5]   STEREOCHEMICAL INVESTIGATIONS OF COORDINATED SULFUR STEREOCENTERS - X-RAY STRUCTURES OF DIASTEREOMERS OF (-)589-[PD((R)-CH3CH(1-C10H6)NME2-C2,N)(R/S)-(PH2PCH2SME-P,S)]PF6 [J].
CHOOI, SYM ;
HOR, TSA ;
LEUNG, PH ;
MOK, KF .
INORGANIC CHEMISTRY, 1992, 31 (08) :1494-1500
[6]   ENANTIOSELECTIVE BIOTRANSFORMATION OF ETHYL-NORMAL-PROPYLARSINIC ACID BY THE MOLD SCOPULARIOPSIS-BREVICAULIS - ASYMMETRIC-SYNTHESIS OF (R)-ETHYLMETHYL-NORMAL-PROPYLARSINE [J].
GUGGER, P ;
WILLIS, AC ;
WILD, SB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) :1169-1170
[7]   MENTHYL-SUBSTITUTED ORGANOPHOSPHORUS COMPOUNDS .6. PREPARATION OF P(L-MEN)RCL AND P(L-MEN)R(S)CL (R = ME, ET, PRI, BUT, OR PH-MEN = CYCLO-C6H9-2-PRI-5-ME) AND NUCLEAR-MAGNETIC-RESONANCE STUDIES OF CONFIGURATION AND HALOGEN EXCHANGE [J].
HAGELE, G ;
KUCKELHAUS, W ;
TOSSING, G ;
SEEGA, J ;
HARRIS, RK ;
CRESWELL, CJ ;
JAGELAND, PT .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1987, (04) :795-805
[8]  
Hall S. R., 1992, XTAL3 2 REFERENCE MA
[9]   ORGANO-PHOSPHORUS COMPOUNDS .93. CHEMISTRY OF OPTICALLY-ACTIVE PHOSPHINOUS ACID-AMIDES [J].
HORNER, L ;
JORDAN, M .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1980, 8 (02) :235-242
[10]   RESOLUTIONS INVOLVING METAL COMPLEXATION - SYNTHESIS AND RESOLUTION OF (+/-)-(2-MERCAPTOETHYL)METHYLPHENYLARSINE - CRYSTAL AND MOLECULAR-STRUCTURE OF (-)589-[PD((R)-CH3CH(1-C10H6)NME2-C2,N)((S)-PHMEASCH2S-AS,MU-S)PDCL((R)-CH3CH(1-C10H6)NME2-C2,N)].0.67CH2CL2 [J].
LEUNG, PH ;
MCLAUGHLIN, GM ;
MARTIN, JWL ;
WILD, SB .
INORGANIC CHEMISTRY, 1986, 25 (19) :3392-3395