Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O′-dibenzoyl-(2R,3R)- or O,O′-di-p-toluoyl-(2R,3R)-tartaric acid

被引：12
|
作者：
Bagi, Peter [1 ]
Kallay, Mihaly [2 ,3 ]
Hessz, Dora [4 ]
Kubinyi, Miklos [3 ,4 ]
Holczbauer, Tamas [5 ]
Czugler, Matyas [5 ]
Fogassy, Elemer [1 ]
Keglevich, Gyoergy [1 ]
机构：
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Phys Chem & Mat Sci, MTA BME Lendulet Quantum Chem Res Grp, H-1521 Budapest, Hungary
[3] Budapest Univ Technol & Econ, Dept Phys Chem & Mat Sci, H-1521 Budapest, Hungary
[4] Hungarian Acad Sci, Res Ctr Nat Sci, Inst Mol Pharmacol, H-1525 Budapest, Hungary
[5] Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, H-1525 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 04期
基金：
匈牙利科学研究基金会;
关键词：
6-MEMBERED P-HETEROCYCLES; ENANTIOSELECTIVE DESYMMETRIZATION; PHOSPHINE OXIDES;
D O I：
10.1016/j.tetasy.2014.01.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
1-n-Propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ('TADDOL') and (-)-(2R,3R)-alpha,alpha,alpha,alpha'-tetraphenyl-1,4-dioxaspiro[4.5]clecan-2,3-dimethanol ('spiro-TADDOL'), as well as the acidic and neutral Ca2+ salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid. In one case, the diastereomeric complex could be identified by single crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by CD spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：318 / 326
页数：9
相关论文
共 50 条
  • [1] Resolution of 1-n-Butyl-3-Methyl-3-Phospholene 1-Oxide With TADDOL Derivatives and Calcium Salts of O, O'-Dibenzoyl-(2R,3R)- or O, O'-di-p-Toluoyl-(2R,3R)- tartaric Acid
    Bagi, Peter
    Fekete, Andras
    Kallay, Mihaly
    Hessz, Dora
    Kubinyi, Miklos
    Holczbauer, Tamas
    Czugler, Matyas
    Fogassy, Elemer
    Keglevich, Gyoergy
    [J]. CHIRALITY, 2014, 26 (03) : 174 - 182
  • [2] (-)-(2R, 3R)-O, O′-dibenzoyl-(2R, 3R)-tartaric acid-hexamethylphosphoramide (1/2)
    Zhang, Yi-Jian
    Shu, Zhan
    Feng, Wen-Jie
    Li, Mei-Chao
    Jin, Zhi-Min
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O1546 - O1548
  • [3] O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent
    H. Simon
    K. Marthi
    Gy. Pokol
    E. Fogassy
    D. Kozma
    [J]. Journal of Thermal Analysis and Calorimetry, 2003, 74 : 155 - 162
  • [4] O,O′-di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent
    Simon, H
    Marthi, K
    Pokol, G
    Fogassy, E
    Kozma, D
    [J]. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2003, 74 (01) : 155 - 162
  • [5] Thermoanalytical Study of O,O'-dibenzoyl-(2R, 3R)-Tartaric Acid SMC
    H. Simon
    Z. Vincze
    K. Marthi
    G. Lévai
    G. Pokol
    E. Fogassy
    D. Kozma
    [J]. Journal of Thermal Analysis and Calorimetry, 2004, 75 : 787 - 793
  • [6] Alcohol-O,O′-dibenzoyl-(2R,3R)-tartaric acid complexes
    Kovári, Z
    Böcskei, Z
    Kassai, C
    Fogassy, ER
    Kozma, D
    [J]. CHIRALITY, 2004, 16 : S23 - S27
  • [7] Coordinative resolution of 1-phenyl- and 1-naphthyl-3-methyl-3-phospholene 1-oxides with calcium hydrogen O,O′-dibenzoyl-(2R,3R)-tartrate or calcium hydrogen O,O′-di-p-toluyl-(2R,3R)-tartrate
    Ujj, Viktoria
    Schindler, Jozsef
    Novak, Tibor
    Czugler, Matyas
    Fogassy, Elemer
    Keglevich, Gyoergy
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (16) : 1973 - 1977
  • [8] Optical resolution of racemic alcohols by diastereoisomeric complex formation with O,O'-dibenzoyl-(2R,3R)-tartaric acid; The crystal structure of the (-)-(1R,2S,5R)-menthol center dot O,O'-dibenzoyl-(2R,3R)-tartaric acid complex
    Kozma, D
    Bocskei, Z
    Kassai, C
    Simon, K
    Fogassy, E
    [J]. CHEMICAL COMMUNICATIONS, 1996, (06) : 753 - 754
  • [9] A Case Study on the Resolution of the 1-i-Butyl-3-methyl-3-phospholene 1-Oxide via Diastereomeric Complex Formation Using TADDOL Derivatives and via Diastereomeric Coordination Complexes Formed from the Calcium Salts of O,O′-Diaroyl-(2R,3R)tartaric Acids
    Bagi, Peter
    Fekete, Andras
    Kallay, Mihaly
    Hessz, Dora
    Kubinyi, Miklos
    Holczbauer, Tamas
    Czugler, Matyas
    Fogassy, Elemer
    Keglevich, Gyoergy
    [J]. HETEROATOM CHEMISTRY, 2015, 26 (01) : 79 - 90
  • [10] Optical resolution of racemic alcohols via diastereoisomeric supramolecular compound formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid
    Kassai, C
    Juvancz, Z
    Bálint, J
    Fogassy, E
    Kozma, D
    [J]. TETRAHEDRON, 2000, 56 (42) : 8355 - 8359
12345