PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE ALLYLAMINATION OF ALLENIC ALCOHOLS

被引：55
|
作者：
KIMURA, M [1 ]
FUGAMI, K [1 ]
TANAKA, S [1 ]
TAMARU, Y [1 ]
机构：
[1] NAGASAKI UNIV,FAC ENGN,DEPT APPL CHEM,BUNKYO KU,NAGASAKI 852,JAPAN
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 24期
关键词：
D O I：
10.1021/jo00050a001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium [PdCl2(PhCN)2 or Pd2(dba)3.CHCl3] catalyzes the reaction of O-(2,3-butadienyl) N-tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted oxazolidin-2-ones 2 in good yields. Under similar conditions, Pd(PPh3)4 catalyzes an N-allylation of 1 to give 3, and chloro-pi-allylpalladium(II) dimer promotes a dimerization of 1g and gives 4 as a major product together with 2.
引用
收藏
页码：6377 / 6379
页数：3
相关论文
共 50 条
  • [1] Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates
    Bäckvall, J.-E. (jeb@organ.su.se), 1600, American Chemical Society (125):
  • [2] Stereoselective palladium-catalyzed carbocyclization of allenic allylic carboxylates
    Franzén, J
    Löfstedt, J
    Falk, J
    Bäckvall, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) : 14140 - 14148
  • [3] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF ALLYLIC AMINES
    TAMARU, Y
    BANDO, T
    KAWAMURA, Y
    OKAMURA, K
    YOSHIDA, Z
    SHIRO, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) : 1498 - 1500
  • [4] REGIOSELECTIVE AND STEREOSELECTIVE PALLADIUM-CATALYZED FUNCTIONALIZATIONS OF DIENES - SYNTHESIS OF (+/-)-SATIVENE
    ANTONSSON, T
    MALMBERG, C
    MOBERG, C
    TETRAHEDRON LETTERS, 1988, 29 (46) : 5973 - 5974
  • [5] REGIOSELECTIVE AND STEREOSELECTIVE PALLADIUM(0) CATALYZED HYDROSTANNATION OF DISUBSTITUTED PROPARGYL ALCOHOLS
    GREEVES, N
    TORODE, JS
    SYNLETT, 1994, (07) : 537 - 538
  • [6] REGIOSELECTIVE AND IN SOME CASES STEREOSELECTIVE CARBONYLATION OF ALPHA-ALLENIC ALCOHOLS TO ALPHA-VINYLACRYLIC ACIDS CATALYZED BY A CATIONIC PALLADIUM COMPLEX
    PIOTTI, ME
    ALPER, H
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08): : 1956 - 1957
  • [7] Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
    Faraoni, Maria A. B.
    Gerbino, Dario C.
    Podesta, Julio C.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (10) : 1877 - 1885
  • [8] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE ARYLDESILYLATION OF ALPHA-SILYLSTYRENES WITH ARENEDIAZONIUM SALTS
    IKENAGA, K
    MATSUMOTO, S
    KIKUKAWA, K
    MATSUDA, T
    CHEMISTRY LETTERS, 1988, (05) : 873 - 876
  • [9] STEREOSELECTIVE AND REGIOSELECTIVE PALLADIUM-CATALYZED 1,4-DIALKOXYLATION OF CONJUGATED DIENES
    BACKVALL, JE
    VAGBERG, JO
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24): : 5695 - 5699
  • [10] Palladium-Catalyzed Regioselective and Stereoselective Oxidative Heck Arylation of Allylamines with Arylboronic Acids
    Zhang, Lingjuan
    Dong, Chaonan
    Ding, Chenjun
    Chen, Jing
    Tang, Weijun
    Li, Huanrong
    Xu, Lijin
    Xiao, Jianliang
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) : 1570 - 1578
12345