Srikrishna, Adusumilli ; Veera Raghava Sharma, G. (1997) Synthesis of chiral tricyclo[3.2.1.02,7]octanes by an efficient 3-exo-trig radical cyclisation reaction Journal of the Chemical Society, Perkin Transactions 1 (2). pp. 177-182. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/content/articlelanding/1997...
Related URL: http://dx.doi.org/10.1039/A601315E
Abstract
Synthesis of chiral tricyclo[3.2.1.02,7]octanes by efficient and exclusive 3-exo-trig radical cyclisation of either a bicyclo[3.2.1]oct-6-en-2-yl radical or a bicyclo[2.2.2]oct-5-en-2-yl radical is described. Reaction of the methoxy enones 7a-c with boron tribromide at low temperature furnishes the bicyclo[3.2.1]octenyl bromides 9a-c and 10a-c along with varying amounts of 8a-c, whereas the methoxy enone 7d provides the unrearranged bicyclo[2.2.2]octenyl bromide 8d. Treatment of the homoallyl bromides 9a-c and 10a-c and 8d with tributyltin hydride and AIBN generates, exclusively, the tricyclic ketones 15a-d.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 48807 |
| Deposited On: | 15 Jul 2011 12:27 |
| Last Modified: | 15 Jul 2011 12:27 |
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