Multicomponent one-pot procedure for the synthesis of free α-chiral amines from aldehydes

被引:42
|
作者
Côté, A [1 ]
Charette, AB [1 ]
机构
[1] Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
来源
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 26期
关键词
D O I
10.1021/jo0516483
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of free a-chiral amines by a one-pot multicomponent procedure from commercially available starting materials is described. This enantioselective reaction involves a catalytic asymmetric addition of dialkylzinc reagents to N-diphenylphosphinoylimines with use of an air-stable precatalyst complex 1. The a-chiral amines are prepared with a one-pot procedure from alkyl and aryl aldehydes in good yield (41-90%) and with excellent enantioselectivity (90-97% ee).
引用
收藏
页码:10864 / 10867
页数:4
相关论文
共 50 条
  • [1] Multicomponent procedure for the catalytic enantioselective synthesis of free α-chiral amines from aldehydes.
    Côté, A
    Charette, AB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U333 - U333
  • [2] A one-pot procedure for the synthesis of iodoalkynes from aldehydes
    Michel, P
    Rassat, A
    TETRAHEDRON LETTERS, 1999, 40 (49) : 8579 - 8581
  • [3] One-pot synthesis of chiral azetidines from chloroaldehyde and chiral amines
    Orr , Suvi T. M.
    Cabral, Shawn
    Fernando, Dilinie P.
    Makowski, Teresa
    TETRAHEDRON LETTERS, 2011, 52 (28) : 3618 - 3620
  • [4] One-Pot Synthesis of Chiral Nonracemic Amines
    Roe, Caroline
    Hobbs, Heather
    Stockman, Robert A.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22): : 9452 - 9459
  • [5] An improved one-pot procedure for the synthesis of alkynes from aldehydes
    Muller, S
    Liepold, B
    Roth, GJ
    Bestmann, HJ
    SYNLETT, 1996, (06) : 521 - &
  • [6] A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes
    Michel, P
    Gennet, D
    Rassat, A
    TETRAHEDRON LETTERS, 1999, 40 (49) : 8575 - 8578
  • [7] One-pot diastereoselective synthesis of α-aminonitriles from aldehydes, chiral amines, and trimethylsilyl cyanide under solvent-free conditions
    Kazemeini, A
    Azizi, N
    Saidi, MR
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (01) : 48 - 51
  • [8] One-pot diastereoselective synthesis of α-aminonitriles from aldehydes, chiral amines, and trimethylsilyl cyanide under solvent-free conditions
    A. Kazemeini
    N. Azizi
    M. R. Saidi
    Russian Journal of Organic Chemistry, 2006, 42 : 48 - 51
  • [9] A one-pot synthesis of tetrahydroisoquinolonic acids from aldehydes and amines in trimethylorthoformate
    Yu, NF
    Poulain, R
    Gesquiere, JC
    SYNLETT, 2000, (03) : 355 - 356
  • [10] Synthesis of Primary Amines by One-Pot Reductive Amination of Aldehydes
    Ayedi, Mohamed Ali
    Le Bigot, Yves
    Ammar, Houcine
    Abid, Souhir
    El Gharbi, Rachid
    Delmas, Michel
    SYNTHETIC COMMUNICATIONS, 2013, 43 (16) : 2127 - 2133