Abstract
Several organocatalysts were tested in the cross condensation of isobutyraldehyde and acetone. Formation of aldol-type and Mannich-type (“aldol condensation”) products was assessed, and Aldol/Mannich proportion studied under several reaction conditions and at different conversions. Organocatalysts able to form Seebach’s oxazolidinones, proline and prolinol, led to high Aldol/Mannich relationships (60−10, depending on organocatalyst, reaction conditions, and conversions), whereas organocatalysts unable to form such oxazolidinones (pyrrolidine, O-methylprolinol and proline tbutyl ester) yielded much lower Aldol/Mannich relationships in all conditions and conversions studied (<2.8). These results suggest that Seebach’s oxazolidinones might act as “controllers” of the reaction, thus partly avoiding the formation of the Mannich-type adducts, by removing activated forms of aldehyde from the catalytic cycle.
Original language | English |
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Pages (from-to) | 70-75 |
Journal | ACS catalysis |
Volume | 1 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2011 |
Externally published | Yes |
Keywords
- n/a OA procedure