Khan, Faiz Ahmed ; Dash, Jyotirmayee (2003) A novel and expeditious approach to unusual spirolactam building blocks Journal of Organic Chemistry, 68 (11). pp. 4556-4559. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo034023i
Related URL: http://dx.doi.org/10.1021/jo034023i
Abstract
A rapid access to 7-azaspiro[4.5]decan-6-ones 1 involving three regio- and chemoselective reactions starting from tetrabromonorbornyl derivatives is described. The alkaline H2O2 cleavage reaction of monosubstituted α-diketones 9 furnished the potential bridged bicyclic lactones 10 in a highly regio- and stereoselective manner. The radical-mediated, intermolecular bridgehead C-C bond formation of the versatile bridged lactones 10 with acrylonitrile followed by LAH reduction of the adduct 13 intriguingly leads to the formation of novel spirolactam building blocks 1.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 79666 |
| Deposited On: | 27 Jan 2012 14:50 |
| Last Modified: | 27 Jan 2012 14:50 |
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