Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2

被引:33
作者
Foo, Siong Wan [1 ]
Takada, Yuki [1 ]
Yamazaki, Yusuke [1 ]
Saito, Susumu [1 ,2 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Inst Adv Res, Nagoya, Aichi 4648601, Japan
关键词
Carbon dioxide; Amino alcohol; Dehydration; Cesium carbonate; Alkali metal carbonate; Oxazolidinone; GAS SHIFT REACTION; HOMOGENOUS RECYCLABLE CATALYST; PROMOTED CU/SIO2 CATALYST; SINGLE-CRYSTAL ELECTRODES; SOLVENT-FREE CONDITIONS; BETA-AMINO ALCOHOLS; FORMIC-ACID; ELECTROCHEMICAL REDUCTION; OXIDATIVE CARBONYLATION; SELECTIVE SYNTHESIS;
D O I
10.1016/j.tetlet.2013.06.100
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dehydrative synthesis of oxazolidinones from amino alcohols and CO2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4717 / 4720
页数:4
相关论文
共 124 条
[61]   Recent advances in the homogeneous hydrogenation of carbon dioxide [J].
Jessop, PG ;
Joó, F ;
Tai, CC .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2425-2442
[62]   HOMOGENEOUS HYDROGENATION OF CARBON-DIOXIDE [J].
JESSOP, PG ;
IKARIYA, T ;
NOYORI, R .
CHEMICAL REVIEWS, 1995, 95 (02) :259-272
[63]   HOMOGENEOUS CATALYTIC-HYDROGENATION OF SUPERCRITICAL CARBON-DIOXIDE [J].
JESSOP, PG ;
IKARIYA, T ;
NOYORI, R .
NATURE, 1994, 368 (6468) :231-233
[64]   Homogeneous catalysis in supercritical fluids: Hydrogenation of supercritical carbon dioxide to formic acid, alkyl formates, and formamides [J].
Jessop, PG ;
Hsiao, Y ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :344-355
[65]   Naturally occurring α-amino acid: a simple and inexpensive catalyst for the selective synthesis of 5-aryl-2-oxazolidinones from CO2 and aziridines under solvent-free conditions [J].
Jiang, Huan-Feng ;
Ye, Jin-Wu ;
Qi, Chao-Rong ;
Huang, Liang-Bin .
TETRAHEDRON LETTERS, 2010, 51 (06) :928-932
[66]   Ceria nanoparticles as heterogeneous catalyst for CO2 fixation by ω-aminoalcohols [J].
Juarez, Raquel ;
Concepcion, Patricia ;
Corma, Avelino ;
Garcia, Hermenegildo .
CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4181-4183
[67]   gem-Disubstituent effect:: Theoretical basis and synthetic applications [J].
Jung, ME ;
Piizzi, G .
CHEMICAL REVIEWS, 2005, 105 (05) :1735-1766
[68]   Effective scCO2-ionic liquid reaction system based on symmetric aliphatic ammonium salts for the rapid CO2 fixation with aziridine to 2-oxazolidinone [J].
Kawanami, H ;
Matsumoto, H ;
Ikushima, Y .
CHEMISTRY LETTERS, 2005, 34 (01) :60-61
[69]   Synthesis of 2-oxazolidinone from β-aminoalcohol using Supercritical carbon dioxide [J].
Kawanami, H ;
Ikushima, Y .
JOURNAL OF THE JAPAN PETROLEUM INSTITUTE, 2002, 45 (05) :321-324
[70]   CARBON-DIOXIDE FIXATION FORMING OXAZOLIDONE COUPLED WITH A THIOL/FE4S4 CLUSTER REDOX SYSTEM [J].
KODAKA, M ;
TOMOHIRO, T ;
LEE, AL ;
OKUNO, HY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (19) :1479-1481