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 50 条
  • [21] Enantioselective Michael addition catalyzed by cinchona alkaloids
    Szöllösi, G
    Bartók, M
    CHIRALITY, 2001, 13 (10) : 614 - 618
  • [22] LITHIUM ALKOXIDES OF CINCHONA ALKALOIDS AS CHIRAL CONTROLLERS FOR ENANTIOSELECTIVE ACETYLIDE ADDITION TO CYCLIC N-ACYL KETIMINES
    HUFFMAN, MA
    YASUDA, N
    DECAMP, AE
    GRABOWSKI, EJJ
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06): : 1590 - 1594
  • [23] Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines
    Huffman, M. A.
    Yasuda, N.
    DeCamp, A. E.
    Grabowski, E. J. J.
    Journal of Organic Chemistry, 60 (06):
  • [24] New approaches to enantioselective fluorination: Cinchona alkaloids combinations and chiral ligands/metal complexes
    Shibata, Norio
    Ishimaru, Takehisa
    Nakamura, Shuichi
    Toru, Takeshi
    JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (05) : 469 - 483
  • [25] Salicylhydrazone ligands for enantioselective addition of diethylzinc to aldehydes
    Arai, Takayoshi
    Endo, Yoko
    Yanagisawa, Akira
    TETRAHEDRON-ASYMMETRY, 2007, 18 (02) : 165 - 169
  • [26] Chiral ligands for asymmetric synthesis:: enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols
    Yun, HY
    Wu, YJ
    Wu, YS
    Ding, KL
    Zhou, Y
    TETRAHEDRON LETTERS, 2000, 41 (52) : 10263 - 10266
  • [27] New chiral ligands derived from (S)-leucine for the enantioselective addition of diethylzinc to aldehydes
    Kawanami, Y
    Mitsuie, T
    Miki, M
    Sakamoto, T
    Nishitani, K
    TETRAHEDRON, 2000, 56 (02) : 175 - 178
  • [28] SOME ASPECTS OF THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY CHIRAL NONRACEMIC PYRIDINE LIGANDS
    FALORNI, M
    GIACOMELLI, G
    GAZZETTA CHIMICA ITALIANA, 1992, 122 (08): : 339 - 340
  • [29] Chiral 1,3-oxazolidines as the ligands for the enantioselective addition of diethylzinc to aryl aldehydes
    Prasad, KRK
    Joshi, NN
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (01): : 150 - 153
  • [30] 3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes
    Karabuga, Semistan
    Karakaya, Idris
    Ulukanli, Sabri
    TETRAHEDRON-ASYMMETRY, 2014, 25 (10-11) : 851 - 855