The dual-catalyzed (amino alcohol Lewis acid) enantioselective addition of diethylzinc to N-diphenylphosphinoyl imines

被引：40
|
作者：
Jimeno, C [1 ]
Vidal-Ferran, A [1 ]
Moyano, A [1 ]
Pericàs, MA [1 ]
Riera, A [1 ]
机构：
[1] Univ Barcelona, Dept Quim Organ, Unitat Reccerca Sintesi Aismetr, E-08028 Barcelona, Spain
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 04期
关键词：
imines; addition reactions; zinc and compounds; asymmetric induction;
D O I：
10.1016/S0040-4039(98)02410-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optimal structural characteristics within a family of (2R,3R)-1-alkoxy-3-dialkylamino-3-phenyl-2-propanols have been determined for maximum enantioselectivity in the addition of diethylzinc to N-diphenylphosphinoyl imines (1-alkoxy = trityloxy; 3-dialkylamino = piperidino). The simultaneous use of silylating agents acting as Lewis acids to induce rate acceleration has been investigated, allowing the identification of triisopropylsilyl chloride and tert-butyldiphenylsilyl chloride as the most efficient mediators in terms of rate enhancement and enantiomeric excess of the resulting phosphinamides. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：777 / 780
页数：4
相关论文
共 16 条
  • [1] 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
  • [2] Enantioselective addition of terminal alkynes to N-(diphenylphosphinoyl)imines catalyzed by Zn-BINOL complexes
    Blay, Gonzalo
    Ceballos, Eric
    Monleon, Alicia
    Pedro, Jose R.
    TETRAHEDRON, 2012, 68 (09) : 2128 - 2134
  • [3] Enantioselective Bronsted acid catalyzed addition reactions of methyleneaminopyrrolidine to imines
    Dixon, DJ
    Tillman, AL
    SYNLETT, 2005, (17) : 2635 - 2638
  • [4] Asymmetric Addition of Terminal Alkynes to N-(Diphenylphosphinoyl)imines Promoted by Stoichiometric Amounts of a Proline-Derived β-Amino Alcohol
    Yan, Wenjin
    Mao, Bin
    Zhu, Shaoqun
    Jiang, Xianxing
    Liu, Zhongli
    Wang, Rui
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) : 3790 - 3794
  • [5] The catalytic asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines catalyzed by Cu(OTf)2-chiral N-(binaphthyl-2-yl)thiophosphoramide ligands
    Shi, M
    Wang, CJ
    ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) : 971 - 973
  • [6] Enantioselective addition of diethylzinc to aldehydes catalyzed by chiral amino alcohols. Substituent effect and nonlinear effect
    Ohga, T
    Umeda, S
    Kawanami, Y
    TETRAHEDRON, 2001, 57 (23) : 4825 - 4829
  • [7] Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes; Addition to Imines and Enones
    Komai, Hirotomo
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    Kanai, Motomu
    SYNTHESIS-STUTTGART, 2012, 44 (14): : 2185 - 2194
  • [8] The chiral N-monosubstituted 1,2-diphenyl-2-aminoethanols promoted enantioselective diethylzinc addition to in situ formed imines
    Yang, WW
    Cun, LF
    Zhi, YG
    Mi, AQ
    Jiang, YZ
    Gong, LZ
    LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (07) : 605 - 607
  • [9] Chiral N-formyl amino alcohol as Lewis basic organocatalyst for enantioselective hydrosilylation of ketimines
    Wang ZhouYu
    Zhou Li
    Lu XiaoXia
    Sun Jian
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1726 - 1728
  • [10] Enantioselective synthesis of β-amino alcohols and α-amino acids via a copper catalyzed addition of diorganozinc reagents to N-phosphinoylimines
    Desrosiers, JN
    Côte, A
    Charette, AB
    TETRAHEDRON, 2005, 61 (26) : 6186 - 6192
12