DETERMINATION OF THE ENANTIOMERIC PURITY AND ABSOLUTE-CONFIGURATION OF ALPHA-HYDROXY PHOSPHONATES

被引：58
|
作者：
KOZLOWSKI, JK [1 ]
RATH, NP [1 ]
SPILLING, CD [1 ]
机构：
[1] UNIV MISSOURI,DEPT CHEM,ST LOUIS,MO 63121
来源：
TETRAHEDRON | 1995年 / 51卷 / 23期
基金：
美国国家科学基金会;
关键词：
D O I：
10.1016/0040-4020(95)00308-U
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The absolute configuration of alpha-hydroxy phosphonates was determined by NMR spectroscopy of the O-methyl mandelate ester derivatives. The O-methyl mandelate ester diastereoisomers are distinguishable by their H-1 and P-31 NMR spectra and the observed chemical shifts allow assignment of the absolute configuration of the phosphonate C-1. The crystal structure of (1R) dimethyl 1-[(2'R)-2'-methoxy-2'-phenylacetoxy]-3-phenyl-2E-propenyl phosphonate was determined by X-ray diffraction. The enatiomers were separable by HPLC on a chiral stationery phase and therefore the enantiomeric purity of the hydroxy phosphonates could accurately be determined.
引用
收藏
页码：6385 / 6396
页数：12
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