A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

被引：21
|
作者：
Aubineau, Thomas [1 ]
Cossy, Janine [1 ]
机构：
[1] PSL Univ, Lab Chim Organ, Inst Chem Biol & Innovat CBI, UMR 8231,ESPCI Paris,CNRS, 10 Rue Vauquelin, F-75231 Paris 05, France
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 23期
关键词：
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; HETEROCYCLES; PIPERAZINES; ACTIVATION;
D O I：
10.1021/acs.orglett.8b03141
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.
引用
收藏
页码：7419 / 7423
页数：5
相关论文
共 50 条
  • [21] A Novel One-Pot Synthesis of Substituted Quinolines
    Sabbagham, Maryam
    Yavari, Issa
    Hossaini, Zinatossadat
    Souri, Sannaz
    HELVETICA CHIMICA ACTA, 2010, 93 (05) : 946 - 950
  • [22] One-pot synthesis of highly substituted indolines
    Liu, Kevin G.
    Lo, Jennifer R.
    Robichaud, Albert J.
    TETRAHEDRON, 2010, 66 (03) : 573 - 577
  • [23] One-pot synthesis of substituted steroidal thiazoles
    Shafiullah, S
    Siddiqui, IH
    Jamaluddin, M
    Khan, EH
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2000, 77 (02) : 102 - 103
  • [24] Diastereoselective One-Pot Synthesis of Tetrafunctionalized 2-Imidazolines
    Janssen, Guido V.
    Slobbe, Paul
    Mooijman, Maurice
    Kruithof, Art
    Ehlers, Andreas W.
    Guerra, Celia Fonseca
    Bickelhaupt, F. Matthias
    Slootweg, J. Chris
    Ruijter, Eelco
    Lammertsma, Koop
    Orru, Romano V. A.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11): : 5219 - 5226
  • [25] Diastereoselective One-Pot Synthesis of Phosphorylated N,N′-Methylenediacrylamides
    Tavakoli, Ziba
    Yavari, Issa
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (04) : 440 - 448
  • [26] One-pot diastereoselective synthesis of new racemic and achiral spirohydantoins
    Mahmoodi, NO
    Khodaee, Z
    MENDELEEV COMMUNICATIONS, 2004, 14 (06) : 304 - 306
  • [27] An Efficient one-pot enantio- and diastereoselective synthesis of heterocycles
    Trost, BM
    Machacek, MR
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) : 4693 - 4697
  • [28] Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit
    Teimouri, Mohammad Bagher
    Asnaashari, Bita
    Moayedi, Maryam
    Naderi, Soheila
    SYNLETT, 2015, 26 (01) : 101 - 107
  • [29] Diastereoselective, one-pot synthesis of γ-amino alcohols from ketimines
    Veenstra, SJ
    Kinderman, SS
    SYNLETT, 2001, (07) : 1109 - 1112
  • [30] A Facile One-Pot Synthesis of Substituted Quinolines via New Multicomponent Reaction
    Rineh, Amir
    Khalilzadeh, Mohammad A.
    Hashemi, Mohammad M.
    Rajabi, Medi
    Karimi, Fatemeh
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 789 - 791
12345