| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5281344 | Tetrahedron Letters | 2010 | 5 Pages |
Abstract
We have designed and synthesized N-arylprolinamides 7-10 with a potential to involve in the binding of electrophilic aldehydes via two N-Hâ¯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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Satyajit Saha, Jarugu Narasimha Moorthy,