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

页码：318 / 326

页数：9

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