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
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 40期
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 50 条
  • [31] The first use of chiral oxazoline ligands in the highly enantioselective diethylzinc addition to diphenylphosphinoyl imines
    Zhang, XM
    Lin, WQ
    Gong, LZ
    Mi, AQ
    Cui, X
    Jiang, YZ
    Choi, MCK
    Chan, ASC
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1535 - 1537
  • [32] Enantioselective addition of diethylzinc to aldehydes using 1,4-aminoalcohols as chiral ligands
    Scarpi, D
    Lo Galbo, F
    Occhiato, EG
    Guarna, A
    TETRAHEDRON-ASYMMETRY, 2004, 15 (08) : 1319 - 1324
  • [33] Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
    Dobrikov, Georgi M.
    Philipova, Irena
    Nikolova, Rositsa
    Shivachev, Boris
    Chimov, Angel
    Dimitrov, Vladimir
    POLYHEDRON, 2012, 45 (01) : 126 - 143
  • [34] The Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by 2-Methylquinoline Derived Chiral Ligands
    Qian Yong XU
    Chinese Chemical Letters, 2001, (05) : 395 - 396
  • [35] Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Chiral Oxazoline-Based Ligands
    A. E. Aydin
    Russian Journal of Organic Chemistry, 2020, 56 : 1304 - 1312
  • [36] Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Chiral Oxazoline-Based Ligands
    Aydin, A. E.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (07) : 1304 - 1312
  • [37] The enantioselective addition of diethylzinc to aldehydes catalyzed by 2-methylquinoline derived chiral ligands
    Xu, QY
    Wang, GX
    Pan, XF
    CHINESE CHEMICAL LETTERS, 2001, 12 (05) : 395 - 396
  • [38] New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes
    Sola, L
    VidalFerran, A
    Moyano, A
    Pericas, MA
    Riera, A
    TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1559 - 1568
  • [39] Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes
    Gou, Shaohua
    Ye, Zhongbin
    Chang, Jing
    Gou, Guangjun
    Feng, Mingming
    APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (06) : 448 - 453
  • [40] Synthesis of new chiral sulfoximidoyl ligands for enantioselective conjugate addition of diethylzinc to enones.
    Kinahan, TC
    Tye, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U195 - U195
12345