New one-pot procedure for the synthesis of diprotected amino alcohols from unprotected vinyl aziridines

被引：5
作者：
Righi, Giuliana [1 ]
Bovicelli, Paolo [2 ]
Tirotta, Ilaria [3 ]
机构：
[1] CNR ICB Unity Rome, I-00185 Rome, Italy
[2] CNR ICB Unity Sassari, I-07040 Sassari, Italy
[3] Univ Roma La Sapienza, Dept Chem, I-00185 Rome, Italy
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 48期
关键词：
Vinyl aziridines; Amino alcohols; Acyl derivatives; Ring opening; Oxazolines; STEREOSELECTIVE-SYNTHESIS; 7-MEMBERED LACTAMS; VINYLAZIRIDINES; ISOMERIZATION; REARRANGEMENT; AZIDOLYSIS; ISOSTERES; ANALOGS; ESTERS; ROUTE;
D O I：
10.1016/j.tetlet.2013.09.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented one-pot reaction that allows the synthesis of diprotected amino alcohols from unprotected vinyl aziridines is reported. The results demonstrate the possibility to use various acyl chlorides in order to obtain differently functionalised fragments. Mechanistic insights are given. (C) 2013 Elsevier Ltd. All rights reserved.
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收藏
页码：6439 / 6442
页数：4
相关论文
共 18 条
  • [1] A new approach to 4-hydroxy-cyclopent-2-en-1-ones by Horner-Wadsworth-Emmons olefination of 1,2-diketones
    Bonadies, F
    Scettri, A
    DiCampli, C
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1899 - 1900
  • [2] Stereospecific Ring Expansion of Chiral Vinyl Aziridines
    Brichacek, Matthew
    Villalobos, Mauricio Navarro
    Plichta, Alexandra
    Njardarson, Jon T.
    [J]. ORGANIC LETTERS, 2011, 13 (05) : 1110 - 1113
  • [3] Asymmetric synthesis of syn hydroxyphenylalanine via aziridine ring expansion to an oxazoline
    Cardillo, G
    Gentilucci, L
    Tolomelli, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (47) : 8261 - 8264
  • [4] Cardillo G, 2000, EUR J ORG CHEM, V2000, P2489
  • [5] α- and β-Substituted phosphonate analogs of LPA as autotaxin inhibitors
    Cui, Peng
    McCalmont, William F.
    Tomsig, Jose L.
    Lynch, Kevin R.
    Macdonald, Timothy L.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) : 2212 - 2225
  • [6] (2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the Caribbean sponge Haliclona vansoesti
    Devijver, C
    Salmoun, N
    Daloze, D
    Braekman, JC
    De Weerdt, WH
    De Kluijver, MJ
    Gomez, R
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (07): : 978 - 980
  • [7] STEREOCHEMISTRY OF ISOMERIZATION N-ACYL-2,3-DISUBSTITUTED AZIRDINES TO DELTA2-OXAZOLINES
    FOGLIA, TA
    GREGORY, LM
    MAERKER, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) : 3779 - &
  • [8] LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P1
  • [9] Lindström UM, 2001, CHEM-EUR J, V7, P94
  • [10] A highly stereoselective aza-[3,3]-Claisen rearrangement of vinylaziridines as a novel entry to seven-membered lactams
    Lindstrom, UM
    Somfai, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (35) : 8385 - 8386
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