Basavaiah, Deevi ; Sreenivasulu, Bandaru ; Rao, Anumolu Jaganmohan (2003) Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives Journal of Organic Chemistry, 68 (15). pp. 5983-5991. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0342424
Related URL: http://dx.doi.org/10.1021/jo0342424
Abstract
The titanium tetrachloride mediated reaction of α-keto esters with 5,5-dimethylcyclohex-2-enone provides the corresponding Baylis-Hillman adducts exclusively whereas a similar reaction of α-keto esters with cyclohex-2-enone furnishes the corresponding aldol adducts (with high syn-diasteroeselectivity) as the major product (along with the Baylis-Hillman adducts as the minor product), thus clearly demonstrating the role of the steric factors in directing the reaction pathway.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 3890 |
| Deposited On: | 18 Oct 2010 09:30 |
| Last Modified: | 17 Jan 2011 04:57 |
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