Synthesis of enantiopure 1,3-oxazolidin-2-ones from α-dibenzylamino esters

被引：5
|
作者：
Ochoa-Teran, Adrian [1 ]
Rivero, Ignacio. A. [1 ]
机构：
[1] Inst Tecnol Tijuana, Ctr Grad & Invest Quim, Apartado Postal 1166, Tijuana 22000, Mexico
来源：
ARKIVOC | 2008年
关键词：
Enantiopure; 1,3-oxazolidin-2-ones; stereoselective addition;
D O I：
10.3998/ark.5550190.0009.e30
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method to obtain enantiopure 5-substituted 1,3-oxazolidin-2-ones 1 from alpha-dibenzylamino esters 2 is reported. This methodology is based on the Lewis acid catalyzed stereoselective addition of trimethylsilyl cyanide to chiral alpha-dibenzylamino aldehydes 3. Magnesium chloride and zinc iodide were tested to catalyze the addition, obtaining higher stereoselectivity with zinc iodide than with magnesium chloride.
引用
收藏
页码：330 / 343
页数：14
相关论文
共 50 条
  • [1] Methods for the synthesis of 1,3-oxazolidin-2-ones (microreview)
    Litvinova, Valeria A.
    Tikhomirov, Alexander S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (11-12) : 733 - 735
  • [2] Diastereoselective Reduction of 1,3-Oxazolidin-2-ones and 1,3-Thiazolidin-2-ones
    Sriharsha, Shimoga Nagaraj
    Shashikanth, Sheena
    Prasad, Beleyur Kamalakar Manu
    Murthy, Srinivas
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2008, 52 (03): : 338 - 340
  • [3] Activation of aldehydes by iridium complexes derived from 1,3-oxazolidin-2-ones
    Padilla, Rosa M.
    Tamariz, Joaquin
    Salazar, Veronica
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [4] Synthesis of new chiral N-arylsulfonyl-1,3-oxazolidin-2-ones from α-amino acids
    Aliyenne, Ahmed Ould
    Kraiem, Jamil
    Kacem, Yakdhane
    Ben Hassine, Bechir
    COMPTES RENDUS CHIMIE, 2007, 10 (03) : 251 - 258
  • [5] Asymmetric reaction of simple nitro compounds with chiral 1,3-oxazolidin-2-ones
    Kudyba, I
    Raczko, J
    Jurczak, J
    HELVETICA CHIMICA ACTA, 2004, 87 (07) : 1724 - 1736
  • [6] Ammonium Ferrate-Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3-Oxazolidin-2-ones
    Panza, Nicola
    Alberti, Matteo
    Galie, Simone
    Damiano, Caterina
    Cargnoni, Fausto
    Trioni, Mario Italo
    Caselli, Alessandro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (40)
  • [7] [inline-graphic not available: see fulltext]Methods for the synthesis of 1,3-oxazolidin-2-ones (microreview)
    Valeria A. Litvinova
    Alexander S. Tikhomirov
    Chemistry of Heterocyclic Compounds, 2023, 59 : 733 - 735
  • [8] Regioselective and stereospecific synthesis of enantiopure 1,3-oxazolidin-2-ones by intramolecular ring opening of 2-(Boc-aminomethyl)aziridines.: Preparation of the antibiotic linezolid
    Moran-Ramalla, Roberto
    Liz, Ramon
    Gotor, Vicente
    ORGANIC LETTERS, 2008, 10 (10) : 1935 - 1938
  • [9] Synthesis and antimicrobial activity of 3-[(4-substituted) (2-oxo-1,3-oxazolidin-3-yl) phosphoryl]-1,3-oxazolidin-2-ones
    Reddy, Mudumala V. N.
    Sankar, A. U. Ravi
    Kumar, B. Siva
    Reddy, C. Suresh
    Raju, C. Naga
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2008, 61 : 43 - 46
  • [10] N-substituted 5-aryl-1,3-oxazolidin-2-ones from arylethylene oxides
    Wrobel, Z.
    Bobin, M.
    Karczewski, R.
    POLISH JOURNAL OF CHEMISTRY, 2006, 80 (06) : 907 - 912
12345