Cationic Rhodium(I)-dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade

被引：35
|
作者：
Tanaka, Ken [1 ]
Okazaki, Eri [1 ]
Shibata, Yu [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 31期
关键词：
DIALLYL-ETHERS; INTERMOLECULAR HYDROACYLATION; ASYMMETRIC ISOMERIZATION; TANDEM; ALDEHYDES; ALLYLAMINES; MECHANISM; VERSATILE; ALCOHOLS;
D O I：
10.1021/ja9038449
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have established that a cationic rhodium(I)-dppf complex catalyzes isomerizations of allyl propargyl ethers to allenic aldehydes in good yields from room temperature to 40 degrees C. On the other hand, carbonyl migration reactions from allenic aldehydes further proceed to give dienals in good yields at 80 degrees C.
引用
收藏
页码：10822 / +
页数：3
相关论文
共 18 条
  • [1] 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
  • [2] Rhodium-Catalyzed Olefin Isomerization/Allyl Claisen Rearrangement/Intramolecular Hydroacylation Cascade
    Okamoto, Ryuichi
    Tanaka, Ken
    ORGANIC LETTERS, 2013, 15 (09) : 2112 - 2115
  • [3] 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
  • [4] Cationic rhodium(I)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones
    Tanaka, K
    Shoji, T
    ORGANIC LETTERS, 2005, 7 (16) : 3561 - 3563
  • [5] Cationic Rhodium(I) Complex-Catalyzed Cotrimerization of Propargyl Esters and Arylacetylenes Leading to Substituted Dihydropentalenes
    Shibata, Yu
    Noguchi, Keiichi
    Tanaka, Ken
    ORGANIC LETTERS, 2010, 12 (23) : 5596 - 5599
  • [6] 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
  • [7] Synthesis of (±)-epi-Jungianol by the Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Hydroarylation Cascade Reaction of Propargyl Vinyl Ethers
    Rinaldi, Antonia
    Lange, Vittoria
    Scarpi, Dina
    Occhiato, Ernesto G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1266 - 1273
  • [8] Synthesis of isoxazoloazaborines via gold(I)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade
    Tsuda, Masato
    Morita, Taiki
    Nakamura, Hiroyuki
    CHEMICAL COMMUNICATIONS, 2022, 58 (12) : 1942 - 1945
  • [9] Cationic Rhodium(I) Complex-Catalyzed [3+2] and [2+1] Cycloadditions of Propargyl Esters with Electron-Deficient Alkynes and Alkenes
    Shibata, Yu
    Noguchi, Keiichi
    Tanaka, Ken
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) : 7896 - +
  • [10] Cationic rhodium(I)/bisphosphine complex-catalyzed cyclization of 1,6-diynes with carboxylic acids
    Tanaka, Ken
    Saitoh, Shunsuke
    Hara, Hiromi
    Shibata, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) : 4817 - 4820
12