Gold-Catalyzed Regiospecific Hydration of N-Tosyl Propargylic Amines

被引:9
作者
Ying, Jun [1 ]
Wang, Hai [1 ]
Qi, Xinxin [1 ]
Peng, Jin-Bao [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
REGIOSELECTIVE HYDRATION; KETONES; ALKYNES; CYCLOISOMERIZATION; DERIVATIVES; CYCLIZATION; 1,6-ENYNES; VERSATILE; STRATEGY; ESTERS;
D O I
10.1021/acs.organomet.8b00549
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A gold-catalyzed regiospecific hydration of N-tosyl propargylic amines has been developed. In the presence of a catalytic amount of the gold catalyst NaAuCl4 center dot 2H(2)O, both alkyl and aryl-substituted N-tosyl propargylic amines were smoothly converted into the corresponding beta-amino ketones with excellent regioselectivities and high yields (up to 85%). Further transformations of the obtained beta-amino ketones to valuable 1,3-amino alcohols were demonstrated as well.
引用
收藏
页码:2837 / 2841
页数:5
相关论文
共 35 条
  • [1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [2] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
  • [3] 2-E
  • [4] N- Propargylamines: versatile building blocks in the construction of thiazole cores
    Arshadi, S.
    Vessally, E.
    Edjlali, L.
    Hosseinzadeh-Khanmiri, R.
    Ghorbani-Kalhor, E.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 625 - 638
  • [5] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    Beller, M
    Seayad, J
    Tillack, A
    Jiao, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
  • [6] Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes
    Colombo, F
    Benaglia, M
    Orlandi, S
    Usuelli, F
    Celentano, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) : 2064 - 2070
  • [7] Rhodium-catalyzed Asymmetric Hydrogenation of -Dehydroamino Ketones: A General Approach to Chiral -amino Ketones
    Gao, Wenchao
    Wang, Qingli
    Xie, Yun
    Lv, Hui
    Zhang, Xumu
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (02) : 231 - 233
  • [8] Regioselective Hydration of Terminal Halo-Substituted Propargyl Carboxylates by Gold Catalyst: Synthesis of α-Acyloxy α′-Halo Ketones
    Ghosh, Nayan
    Nayak, Sanatan
    Prabagar, B.
    Sahoo, Akhila K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (06) : 2453 - 2462
  • [9] Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B
    Ghosh, Nayan
    Nayak, Sanatan
    Sahoo, Akhila K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) : 500 - 511
  • [10] A Versatile and One-Pot Strategy to Synthesize α-Amino Ketones from Benzylic Secondary Alcohols Using N-Bromosuccinimide
    Guha, Somraj
    Rajeshkumar, Venkatachalam
    Kotha, Surya Srinivas
    Sekar, Govindasamy
    [J]. ORGANIC LETTERS, 2015, 17 (03) : 406 - 409