Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazines with (S)-naproxen

被引：54

作者：

Charushin, VN

Krasnov, VP

Levit, GL

Korolyova, MA

Kodess, MI

Chupakhin, ON

Kim, MH

Lee, HS

Park, YJ

Kim, KC

机构：

[1] Russian Acad Sci, Ural Div, Inst Organ Synth, Ekaterinburg 620219, Russia

[2] Urals State Tech Univ, Organ Chem Lab, Ekaterinburg 620002, Russia

[3] Samsung Adv Inst Technol, Taejon 305380, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(99)00276-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A very effective method for the preparation of the (S)-enantiomers of 2,3-dihydro-3-methyl- and 7,8-difluoro-2,3-dihydro-3-methyl-4H- 1,4-benzoxazines (1a and 2a) was developed using (S)-(+)-naproxen acyl chloride as the chiral agent for kinetic resolution of racemates. This method enables one to obtain the (S)-enantiomers of benzoxazines 1a and 2a of high enantiomeric purity (99% ee) in nearly 50% yield, taking into account that the (R)-enantiomers are recycled after their racemisation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2691 / 2702

页数：12

共 17 条

[1] ASYMMETRIC REDUCTION OF 7,8-DIFLUORO-3-METHYL-2H-1,4-BENZOXAZINE - SYNTHESIS OF A KEY INTERMEDIATE OF (S)-(-)-OFLOXACIN (DR-3355) [J].