Enantioselective addition of diethylzinc to a N-diphenylphosphinoylimine employing cinchona alkaloids as chiral ligands

被引:20
作者
Beresford, KJM [1 ]
机构
[1] De Montfort Univ, Sch Pharm, Leicester LE1 9BH, Leics, England
关键词
N-diphenylphospinoylimine; cinchona alkaloids; diethylzinc; enantioselective addition;
D O I
10.1016/S0040-4039(02)01669-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of cinchona alkaloids to promote the addition of diethylzine to P,P-diphenyl-N-(phenylmethylene)phosphinic amide has been examined. Using cinchonine and cinchonidine as ligands, the S and R enantiomers of N-(1-phenylpropyl)-P,P-diphenylphosphinic amide were prepared in good yield with up to 93% ee. The reaction was shown to proceed with catalytic amounts of ligand. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7175 / 7177
页数:3
相关论文
共 12 条
  • [1] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines
    Andersson, PG
    Guijarro, D
    Tanner, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7364 - 7375
  • [2] Jacques J., 1981, Enantiomers, Racemates and Resolutions
  • [3] THE TITANIUM TETRACHLORIDE INDUCED SYNTHESIS OF N-PHOSPHINOYLIMINES AND N-SULPHONYLIMINES DIRECTLY FROM AROMATIC-ALDEHYDES
    JENNINGS, WB
    LOVELY, CJ
    [J]. TETRAHEDRON, 1991, 47 (29) : 5561 - 5568
  • [4] The dual-catalyzed (amino alcohol Lewis acid) enantioselective addition of diethylzinc to N-diphenylphosphinoyl imines
    Jimeno, C
    Vidal-Ferran, A
    Moyano, A
    Pericàs, MA
    Riera, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (04) : 777 - 780
  • [5] Catalytic enantioselective addition to imines
    Kobayashi, S
    Ishitani, H
    [J]. CHEMICAL REVIEWS, 1999, 99 (05) : 1069 - 1094
  • [6] THE INFLUENCE OF ATROPISOMERISM AND CHIRAL CENTER ON THE BIOLOGICAL-ACTIVITY OF METOLACHLOR
    MOSER, H
    RIHS, G
    SAUTER, H
    [J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1982, 37 (04): : 451 - 462
  • [7] PINTO P, 2001, TETRAHEDRON, V57, P1615
  • [8] PHOSPHINAMIDES - A NEW CLASS OF AMINO PROTECTING GROUPS IN PEPTIDE-SYNTHESIS
    RAMAGE, R
    HOPTON, D
    PARROTT, MJ
    KENNER, GW
    MOORE, GA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (06): : 1357 - 1370
  • [9] Asymmetric synthesis of N-diphenylphosphinoylamines by solvent-free enantioselective addition of dialkylzincs to N-diphenylphosphinoylimines
    Sato, I
    Kodaka, R
    Soai, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22): : 2912 - 2914
  • [10] STEREOSELECTIVE ADDITION-REACTION OF DIETHYLZINC TO ALDEHYDES, CATALYZED BY CINCHONA ALKALOIDS
    SMAARDIJK, AA
    WYNBERG, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) : 135 - 137