Synthesis of Substituted Aziridine from (1S,2S)-2-Amino-1- (4-Nitrophenyl)- 1,3-Propanediol

被引：0
|
作者：
Yang Shao-rong1
2.College of Chemistry
机构：
来源：
Wuhan University Journal of Natural Sciences | 2000年 / 03期
关键词：
aziridines; synthesis; chloramphenicol;
D O I：
暂无
中图分类号：
O621.34 [];
学科分类号：
070303 ; 081704 ;
摘要：
S, 3R)-2-acetooxymethanyl-3-(P-nitrophenyl)-N-tosylaz iridine 5 was synthesized from (1S, 2S)-2-amino-1- (4-nitrophenyl)-1, 3-propaned iol 1 in four steps with a 24.8% overall yield. This reaction is ste reospecific and occ urs an expectable configuration inversion at α-carbon atom of benzyl group. Th e structure of substituted aziridine was determined on FT-IR, NMR, MS and so on .
引用
收藏
页码：345 / 347
页数：3
相关论文
共 50 条
  • [21] Electroreduction of (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives. Behaviour of electrogenerated species and applications to organic synthesis
    C.V. Cristea
    C. Moinet
    M. JITARU
    M. Darabantu
    Journal of Applied Electrochemistry, 2005, 35 : 845 - 849
  • [22] (1S,2S)-2-amino-1-phenyl-1,3-propanediol, a spin off from chloramphenicol manufacture, as chiral synthon for (1S,2S)-pseudoephedrine and (R)-phenylalaninol
    Akamanchi, KG
    Ranbhan, KJ
    Shah, BL
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (04): : 293 - 302
  • [23] A novel and simple synthesis of (1S, 2S)-2-amino-1-(p-nitrophenyl)-3-trityloxypropanol
    Yuan, JL
    Dai, HF
    Chen, FE
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (02) : 164 - 166
  • [24] Novel N-modified glycines based on a (1S,2S)-2-amino-1-(4-nitrophenyl) propane-1,3-diol skeleton: 1,3-dioxanes and tripodands
    Moldovan, Oana
    Albert, Katalin
    Nagy, Iulia
    Morar, Cristina
    Sacalis, Carmen
    Darabantu, Mircea
    TETRAHEDRON LETTERS, 2016, 57 (51) : 5808 - 5811
  • [25] Formation of nitrobenzene dimers in racemic and chiral salts of 2-amino-1-(4-nitrophenyl)-1,3-propanediol (ANPD) with oxalic and fumaric acids
    Batisai, Eustina
    Venter, Gerhard A.
    Bathori, Nikoletta B.
    JOURNAL OF MOLECULAR STRUCTURE, 2021, 1224
  • [26] Diastereoselective reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3- propanediol with aromatic aldehydes. Synthesis of (1R,2R,4S,5S,8S)-2,8-diaryl-4- (4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octanes
    Madesclaire M.
    Coudert P.
    Gaumet V.
    Zaitsev V.P.
    Zaitseva Yu.V.
    Chemistry of Heterocyclic Compounds, 2006, 42 (5) : 665 - 670
  • [27] Reaction of (1S,2S)-2-amino-1-phenyl-1,3-propanediol with thioacids under the Mitsunobu reaction condition
    Rozwadowska, MD
    TETRAHEDRON, 1997, 53 (30) : 10615 - 10622
  • [28] A high-yielding synthetic method for the condensates of threo-(1S,2S)-2-amino-1-4'-nitrophenyl-1,3-propanediol and some ketones
    Shan, Z.-X.
    Wan, B.-Y.
    Wang, G.-P.
    Wuhan Daxue Xuebao/Journal of Wuhan University, 2001, 47 (02): : 165 - 168
  • [29] (1S*,2S*)-(+)-2-amino-1-[4-(methylsulfanyl)phenyl]propane-1,3-diol
    Samas, B
    Macikenas, D
    Blackburn, AC
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2793 - O2794
  • [30] Chiral discrimination promoted by (1S,2S)-1-phenyl-2-amino-1,3-propanediol derivatives in the asymmetric reformatsky reaction
    Mastantuono, A
    Pini, D
    Rolfini, C
    Salvadori, P
    CHIRALITY, 1995, 7 (07) : 499 - 504
12345