Stereoselective intramolecular oxazine formation by a π-allylpalladium complex catalyzed by Pd0

被引：13
|
作者：
Joo, Jae-Eun [1 ]
Lee, Kee-Young [1 ]
Pham, Van-Thoai [1 ]
Ham, Won-Hun [1 ]
机构：
[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 10期
关键词：
stereoselective synthesis; chiral oxazine; catalysis; amino alcohol; palladium; synthetic methods;
D O I：
10.1002/ejoc.200600927
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient procedure for synthesizing oxazines was developed by the palladium (0) -catalyzed intramolecular cyclization of a benzamide through a pi-allylpalladium(II) complex. Unlike other palladium-catalyzed reactions, the temperature was found to be a key factor in determining the stereochemistry of the oxazine. ((c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码：1586 / 1593
页数：8
相关论文
共 50 条
  • [41] Oxidative cleavage of tetraaryltetraphosphane-1,4-diides by nickel(II) and palladium(II): Formation of unusual Ni0 and Pd0 diaryldiphosphene complexes
    Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
    Dalton Trans., 2007, 48 (5678-5683):
  • [42] Facile oxidative addition of the phosphorous-selenium bond to Pd(0) and Pt(0) complexes and development of Pd-catalyzed regio- and stereoselective selenophosphorylation of alkynes
    Han, LB
    Choi, N
    Tanaka, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) : 7000 - 7001
  • [43] Allylation of prochiral C-nucleophiles catalyzed by the Pd(0)—(S)-(—)-BINAP complex
    A. V. Lozanova
    T. M. Ugurchieva
    V. V. Veselovsky
    Russian Chemical Bulletin, 2008, 57 : 1787 - 1789
  • [44] Hydrocarbobutoxylation of heptene-1 catalyzed by a Pd(0) complex in the presence of methanesulfonic acid
    Kron, T.E.
    Petrov, E.S.
    Neftekhimiya, 2003, 43 (06): : 412 - 417
  • [45] Allylation of prochiral C-nucleophiles catalyzed by the Pd(0)-(S)-(-)-BINAP complex
    Lozanova, A. V.
    Ugurchieva, T. M.
    Veselovsky, V. V.
    RUSSIAN CHEMICAL BULLETIN, 2008, 57 (08) : 1787 - 1789
  • [46] Hydrocarbobutoxylation of heptene-1 catalyzed by a Pd(0) complex in the presence of methanesulfonic acid
    Kron, TE
    Petrov, ES
    PETROLEUM CHEMISTRY, 2003, 43 (06) : 375 - 378
  • [47] Rate and mechanism of the oxidative addition of phenyl iodide to Pd0 ligated by triphenylarsine:: Evidence for the formation of a T-shaped complex [PhPdI(AsPh3)] and for the decelerating effect of CH2=CH-SnBu3 by formation of [Pd0(η2-CH2=CH-SnBu3)(AsPh3)2]
    Amatore, C
    Bucaille, A
    Fuxa, A
    Jutand, A
    Meyer, G
    Ntepe, AN
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (10) : 2134 - 2142
  • [48] Stereoselective Pd(0) catalysed five component cascade synthesis of complex Z,Z-bisallylamines
    Grigg, Ronald
    Akkarasamiyo, Sunisa
    Chuanopparat, Nutthawat
    Elboray, Elghareeb E.
    Aly, Moustafa F.
    Abbas-Temirek, Hussien H.
    Kongkathip, Boonsong
    Kongkathip, Ngampong
    CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 2007 - 2009
  • [49] Pd(0)-Catalyzed Direct Inter- and Intramolecular C-H Functionalization of 4-Carboxyimidazoles
    Frippiat, Steven
    Peresson, Antoine
    Perse, Thibaut
    Ramondenc, Yvan
    Schneider, Cedric
    Querolle, Olivier
    Angibaud, Patrick
    Poncelet, Virginie
    Meerpoel, Lieven
    Levacher, Vincent
    Bischoff, Laurent
    Baudequin, Christine
    Hoarau, Christophe
    SYNLETT, 2020, 31 (10) : 1015 - 1021
  • [50] The Total Synthesis of the Crinine Alkaloid Hamayne via a Pd[0]-Catalyzed Intramolecular Alder-Ene Reaction
    Petit, Laurent
    Banwell, Martin G.
    Willis, Anthony C.
    ORGANIC LETTERS, 2011, 13 (21) : 5800 - 5803
12345