Optical Resolution of Dimethyl α-Hydroxy-Arylmethylphosphonates via Diastereomer Complex Formation Using Calcium Hydrogen O,O′-Dibenzoyl-(2R,3R)-Tartrate; X-Ray Analysis of the Complexes and Products

被引：3
|
作者：
Radai, Zita [1 ]
Bagi, Peter [1 ]
Czugler, Matyas [1 ]
Karaghiosoff, Konstantin [2 ]
Keglevich, Gyorgy [1 ]
机构：
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary
[2] Ludwig Maximilians Univ Munchen, Dept Chem & Biochem, D-81377 Munich, Germany
来源：
SYMMETRY-BASEL | 2020年 / 12卷 / 05期
关键词：
alpha-hydroxy arylmethylphosphonates; optical resolution; optical isomers; X-ray crystallography; stereostructure; intermolecular interactions; H-bonding; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; ASYMMETRIC HYDROPHOSPHONYLATION; COORDINATIVE RESOLUTION; HYDROXYPHOSPHONATES; EFFICIENT; ACID; HYDROXYALKANEPHOSPHONATES; ANTIBACTERIAL; DERIVATIVES; ALDEHYDES;
D O I：
10.3390/sym12050758
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
Two dimethyl alpha -hydroxy-arylmethylphosphonates (aryl = Ph and 2-MeOPh) were subjected to optical resolution via diastereomer complex formation applying the acidic calcium salt of O,O ' -dibenzoyl-(2R,3R)-tartaric acid as the resolving agent. The dominating diastereomer complexes, whose structure was determined by single crystal X-ray measurements, were obtained in 96% and 68% diastereomer excess values, respectively. After decomposing the diastereomer formations by extraction, and after recrystallizations, the major enantiomer (S and R, respectively) of the alpha -hydroxyphosphonates were prepared in enantiomeric excess values of 96% and 68%, respectively. The stereostructure of the two alpha -hydroxy-arylmethylphosphonates was again established by X-ray measurements. Detailed study on the X-ray data allowed valuable conclusions on the nature of the coordination in the complexes (intermolecular interactions), and on the H-bonding.
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  • [1] 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
  • [2] 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
  • [3] 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
  • [4] 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
    Bagi, Peter
    Kallay, Mihaly
    Hessz, Dora
    Kubinyi, Miklos
    Holczbauer, Tamas
    Czugler, Matyas
    Fogassy, Elemer
    Keglevich, Gyoergy
    [J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (04) : 318 - 326
  • [5] A new optical resolution method: Coordinative resolution of mandelic acid esters. The crystal structure of calcium hydrogen (2R,3R)-O,O'-dibenzoyl tartrate-2(R)-(-)-methyl mandelate
    Mravik, A
    Bocskei, Z
    Katona, Z
    Markovits, I
    Pokol, G
    Menyhard, DK
    Fogassy, E
    [J]. CHEMICAL COMMUNICATIONS, 1996, (16) : 1983 - 1984
  • [6] THE OPTICAL RESOLUTION OF 3-(2'-HYDROXY-2'-PHENYLETHYL)-2-THIAZOLIDINIMINE, AND THE CRYSTAL-STRUCTURE OF THE (2R,3R)-O,O'-DIBENZOYL HYDROGEN TARTRATE SALT OF THE (S)-(+)-ENANTIOMER
    MARTHI, K
    LARSEN, S
    ACS, M
    BALINT, J
    FOGASSY, E
    [J]. ACTA CHEMICA SCANDINAVICA, 1995, 49 (01): : 20 - 27
  • [7] 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
  • [8] Isomer and enantiomer separation of 2-and 4-alkyl-cyclohexanols by stereoselective complex formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid
    Kassai, C
    Bálint, J
    Juvancz, Z
    Fogassy, E
    Kozma, D
    [J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (11) : 1715 - 1719
  • [9] Optical resolution of 2-(2'-hydroxyethylamino)-1-phenylethanol, and the crystal structures of two polymorphic modifications of the (2R,3R)-O,O'-dibenzoyl hydrogen tartrate salt of the (S)-(+)-enantiomer
    Marthi, K
    Larsen, S
    Acs, M
    Balint, J
    Fogassy, E
    [J]. ACTA CHEMICA SCANDINAVICA, 1997, 51 (03): : 367 - 378
  • [10] Enantio selective extraction of D,L-tryptophan by a new chiral selector:: Complex formation with di(2-ethylhexyl)phosphoric acid and O,O′-dibenzoyl-(2R,3R)-tartaric acid
    Tan, B
    Luo, GS
    Qi, X
    Wang, JD
    [J]. SEPARATION AND PURIFICATION TECHNOLOGY, 2006, 49 (02) : 186 - 191
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