Kinetic resolution of 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine derivatives by lipase-catalyzed enantiomer selective acylation

被引：9
|
作者：
Bálint, J
Kiss, V
Egri, G
Kálai, T
Demeter, A
Balog, M
Fogassy, E
Hideg, K
机构：
[1] Univ Pecs, Inst Organ & Med Chem, H-7602 Pecs, Hungary
[2] Tech Univ Budapest, Dept Organ Chem Technol, H-1521 Budapest, Hungary
[3] Gedeon Richter Chem Works Ltd, Spectroscop Res Div, H-1475 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期
基金：
匈牙利科学研究基金会;
关键词：
D O I：
10.1016/j.tetasy.2003.12.026
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Three chiral stable free radicals containing a hydroxymethyl group have been resolved by biocatalysis. By recrystallization and/or re-esterification each molecule was produced in very high enantiomeric purity. The resolved 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine alcohols were converted to methanethiosulfonate spin labels, 1-oxyl-3-methanesulfonylthiomethyl-2,2,5,5-tetramethylpyrrolidines. Enantiomeric purities have been determined by the F-19 NMR method of the respective Mosher esters. Absolute configurations were assigned by comparing the chemical shifts of the Mosher esters and also by comparing the specific rotations obtained with the same enzyme preparations. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：671 / 679
页数：9
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