Saha, Satyajit ; Narasimha Moorthy, Jarugu (2010) Highly enantioselective aldol reactions using N-arylprolinamides with enhanced acidity and double H-bonding potential Tetrahedron Letters, 51 (6). pp. 912-916. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.12.014
Abstract
We have designed and synthesized N-arylprolinamides 7-10 with a potential to involve in the binding of electrophilic aldehydes via two N-H···O hydrogen bonds for application in organocatalytic aldol reactions. The catalyst 10 is shown to afford aldol products in excellent isolated yields with very high diastereo-and enantioselectivites. In addition to enhanced acidity and double hydrogen bonding, the stacking interactions of the p-toluenesulfonyl ring in 10 with the electrophilic aldehyde are proposed to stabilize the transition state.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 60732 |
| Deposited On: | 10 Sep 2011 11:41 |
| Last Modified: | 10 Sep 2011 11:41 |
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