Copper-catalyzed cyclopropanation of 1,2,3,4-tetrahydropyridin-2-ones with diazoacetates - A facile and stereoselective synthesis of 3-oxo-2-azabicyclo [4.1.0] heptanes

被引：4
|
作者：
Jain, SL [1 ]
Sain, B [1 ]
机构：
[1] Indian Inst Petr, Chem & Biosci Div, Dehra Dun 248005, Uttar Pradesh, India
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 212卷 / 1-2期
关键词：
cycloaddition; copper; catalysis; diazocompounds; heterocycles;
D O I：
10.1016/j.molcata.2003.11.008
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The reactions of a series of 1,2,3,4-tetrahydropyridin-2-ones (1) with diazoacetates (2) in the presence of copper-bronze catalyst yielded exclusively 3-oxo-2-azabicyclo [4.1.0] beptanes (3 and 4) in excellent yields with high exo-selectivity. Tetrahydropyridin-2-ones (1) with N-alkyl substituents were found to be more reactive than N-aryl substitutents. Among the various copper catalysts studied, copper(II) triflate was found to be the best catalyst while rhodium chloride, ruthenium chloride did not catalyze the reaction. The application of ultrasonic radiation enhanced the reaction rate and allowed the reactions to be conducted at room temperature. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码：91 / 98
页数：8
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