Cationic rhodium(I)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones

被引：48
|
作者：
Tanaka, K [1 ]
Shoji, T [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 16期
关键词：
D O I：
10.1021/ol051335u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a cationic rhodium(l)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to alpha,beta-enones. The asymmetric variant of this reaction, a kinetic resolution of secondary propargylic alcohols, was also developed with good selectivity. The mechanistic study revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways.
引用
收藏
页码：3561 / 3563
页数：3
相关论文
共 50 条
  • [1] Cationic rhodium(I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones
    Tanaka, Ken
    Shoji, Takeaki
    Hirano, Masao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) : 2687 - 2699
  • [2] CATIONIC RHODIUM(I) COMPLEX-CATALYZED ASYMMETRIC ISOMERIZATION OF ALLYLAMINES TO OPTICALLY-ACTIVE ENAMINES
    TANI, K
    YAMAGATA, T
    OTSUKA, S
    AKUTAGAWA, S
    KUMOBAYASHI, H
    TAKETOMI, T
    TAKAYA, H
    MIYASHITA, A
    NOYORI, R
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) : 600 - 601
  • [3] Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols
    Maeda, Y
    Kakiuchi, N
    Matsumura, S
    Nishimura, T
    Kawamura, T
    Uemura, S
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19): : 6718 - 6724
  • [4] ISOMERIZATION OF PROPARGYLIC ALCOHOLS CATALYZED BY AN IRIDIUM COMPLEX
    MA, DW
    LU, XY
    TETRAHEDRON LETTERS, 1989, 30 (16) : 2109 - 2112
  • [5] A New Route to Substituted Phenols by Cationic Rhodium(I)/BINAP Complex-Catalyzed Decarboxylative [2+2+2] Cycloaddition
    Hara, Hiromi
    Hirano, Masao
    Tanaka, Ken
    ORGANIC LETTERS, 2009, 11 (06) : 1337 - 1340
  • [6] Cationic Rhodium(I)-dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade
    Tanaka, Ken
    Okazaki, Eri
    Shibata, Yu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) : 10822 - +
  • [7] A SELECTIVE SYNTHESIS OF (E)-VINYLSILANES BY CATIONIC RHODIUM COMPLEX-CATALYZED HYDROSILYLATION OF 1-ALKYNES AND TANDEM HYDROSILYLATION ISOMERIZATION REACTION OF PROPARGYLIC ALCOHOLS TO BETA-SILYL KETONES
    TAKEUCHI, R
    NITTA, S
    WATANABE, D
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10): : 3045 - 3051
  • [8] Cationic rhodium(I) complex-catalyzed σ- and π-bond activation cascade: Isomerization of allyl propargyl ethers to allenic aldehydes and dienals
    Tanaka, Ken
    Okazaki, Eri
    Shibata, Yu
    PURE AND APPLIED CHEMISTRY, 2010, 82 (07) : 1453 - 1460
  • [9] Oxovanadium complex-catalyzed oxidation of propargylic alcohols using molecular oxygen
    Maeda, Y
    Kakiuchi, N
    Matsumura, S
    Nishimura, T
    Uemura, S
    TETRAHEDRON LETTERS, 2001, 42 (50) : 8877 - 8879
  • [10] RHODIUM(I)-CATALYZED BIPHASIC ISOMERIZATION OF ALLYLIC ALCOHOLS
    ALPER, H
    HACHEM, K
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11): : 2269 - 2270
12345