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

被引：12

作者：

Bagi, Peter ^{[1
]}

Fekete, Andras ^{[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, Inst Mat & Environm Chem, Res Ctr Nat Sci, H-1519 Budapest, Hungary

[5] Hungarian Acad Sci, Inst Organ Chem, Res Ctr Nat Sci, H-1519 Budapest, Hungary

来源：

HETEROATOM CHEMISTRY | 2015年 / 26卷 / 01期

基金：

匈牙利科学研究基金会;

关键词：

OPTICAL RESOLUTION; ABSOLUTE-CONFIGURATION; ORGANIC DERIVATIVES; P-HETEROCYCLES; PHOSPHORUS; STEREOCHEMISTRY; LIGANDS; PHOSPHINES; CHEMISTRY;

D O I：

10.1002/hc.21218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The resolution of 1-i-butyl-3-methyl-3-phospholene 1-oxide was studied applying TADDOL [(-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane], spiro-TADDOL [(-)-(2R,3R)-,,,-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol], or the acidic and neutral Ca2+ salts of (-)-O,O-dibenzoyl- and (-)-O,O-di-p-toluoyl-(2R,3R)-tartaric acid as the resolving agent. The absolute configuration of the P-asymmetric center was determined by circular dichroism spectroscopy and related quantum chemical calculations. In one instance, the single crystal of the diastereomeric complex incorporating i-butyl-3-phospholene oxide and spiro-TADDOL was subjected to X-ray analysis, which suggested a feasible hypothesis for the efficiency of the resolution process under discussion that may be an example for the solvent-inhibited resolution.

引用

页码：79 / 90

页数：12

共 5 条

[1] 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
[2] 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
[3] 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
[4] 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
[5] 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
Radai, Zita
Bagi, Peter
Czugler, Matyas
Karaghiosoff, Konstantin
Keglevich, Gyorgy
[J]. SYMMETRY-BASEL, 2020, 12 (05):

← 1 →