Yadav, Veejendra K. ; Sriramurthy, V. (2001) A detailed ab initio MO investigation of the diastereoselectivities of five- and six-membered ring ketones bearing O and S, C and S, and C and O substituents at the α-carbon Tetrahedron, 57 (18). pp. 3987-3995. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)00276-9
Abstract
The steric effects in the geometry on cation-chelation predict the experimental π-selectivity of 1-oxa-4-thiaspiro[4.5]decan-6-one, 1-oxa-4-thiaspiro[4.4]nonan-6-one, 1-thiaspiro[4.4] nonan-6-one, and 1-oxaspiro[4.4]nonan-6-one. The reversal in the selectivity of 1-oxa-4-thiaspiro[4.4]nonan-6-one on reduction with (i-Bu)2AlH appears to be a direct consequence of the steric interactions arising from the large i-Bu substituents. The antiperiplanar effects are not as significant as the steric effects.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Facial Selection; Cation-complexation; Antiperiplanar Interactions; Steric Effects |
| ID Code: | 58236 |
| Deposited On: | 31 Aug 2011 06:53 |
| Last Modified: | 31 Aug 2011 06:53 |
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