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
IR@IIP: CSIR-Indian Institute of Petroleum, Dehradun
View Archive Info| Field | Value | |
| Creator |
Jain, Suman L
Sain, Bir |
|
| Date |
2009-06-19T09:12:20Z
2009-06-19T09:12:20Z 2009-06-19T09:12:20Z |
|
| Identifier |
http://hdl.handle.net/123456789/197
|
|
| Description |
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] heptanes (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.
Keywords: Cycloaddition; Copper; Catalysis; Diazocompounds; Heterocycles
|
|
| Language |
en_US
|
|
| Subject |
Cycloaddition
Copper Catalysis Diazocompounds Heterocycles |
|
| Title |
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
|
|
| Type |
Article
|
|