Simple and highly diastereoselective synthesis of trifluoromethyl-containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione

被引：29
|
作者：
Ohkura, H [1 ]
Berbasov, DO [1 ]
Soloshonok, VA [1 ]
机构：
[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 11期
关键词：
kinetic/thermodynamic diastereoselectivity; epimerization; fluorine-containing compounds; 1,3-proton shift;
D O I：
10.1016/S0040-4039(03)00244-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2'-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3R*,5S*)-diastereoselectivity. The thermodynamic (3R*,5R*) diastercomer was prepared as a major product (90% de) by epimerization of the kinetic (3R*,5S*) diastereomer with triethylamine. (C) 2003 Elsevier Science Ltd. All rights reserved.
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收藏
页码：2417 / 2420
页数：4
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