Shinisha, C. B. ; Sunoj, Raghavan B. (2010) The pivotal role of chelation as a stereochemical control element in non-Evans antialdol product formation Organic Letters, 12 (12). pp. 2868-2871. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol100969f
Related URL: http://dx.doi.org/10.1021/ol100969f
Abstract
The origin of stereoselective formation of Evans syn and non-Evans anti aldol products in the reaction between titanium enolate derived from N-succinyloxazolidinone and benzaldehyde is established by using transition-state modeling. The chelated transition-state model is found to hold the key to otherwise less likely non-Evans anti aldol product, whereas the nonchelated model offers a convincing rationalization toward Evans syn aldol product. The computed results are in agreement with the reported experimental observations.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 109785 |
| Deposited On: | 02 Aug 2017 11:53 |
| Last Modified: | 02 Aug 2017 11:53 |
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