Toueg, J. and Prunet, J. (2008) Dramatic solvent effect on the diastereoselectivity of Michael addition: study toward the synthesis of the ABC ring system of hexacyclinic acid. Organic Letters, 10(1), pp. 45-48. (doi: 10.1021/ol702566c)
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Publisher's URL: http://pubs.acs.org
Abstract
During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we have observed a dramatic influence of the solvent on both our key steps. The diastereoselectivity of the intermolecular Michael addition could be totally reversed by changing the polarity of the solvent, and trifluoroethanol was found to be the optimal solvent for the following Mn(III)-promoted radical cyclization
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Prunet, Dr Joelle |
| Authors: | Toueg, J., and Prunet, J. |
| Subjects: | Q Science > QD Chemistry |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Organic Letters |
| Journal Abbr.: | Org. Lett. |
| ISSN: | 1523-7060 |
| ISSN (Online): | 1523-7052 |
| Published Online: | 04 December 2007 |
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