ORGN 51 |
| Organocatalysis of aldol-type processes via an enamine activation manifold has been amply demonstrated with centrally chiral 2°-amines (e.g. 1 and 2, Figure 1). By contrast, few axially chiral 2°-amines have been investigated for the same purpose; Maruoka's binaphthylamines (e.g. 3) represent rare and highly successful examples. In pursuit of new ambifunctional molecules for catalysis in which complementary functional groups flank biaryl quadrants, we have discovered a simple biphenyl derivative, 2',6-dimethoxy-N-methyl-6'-[(methylamino)methyl]-1,1'-biphenyl-2-carboxamide (4), which mediates various carbonyl addition reactions. The serendipitous discovery of amidoamine 4, its concise synthesis from m-anisic acid (4 steps), and its evaluation in direct aldol, Mannich, and Michael reactions will be presented.
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New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 258B, Oral
Division of Organic Chemistry |
