| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
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| Outline of Final Research Achievements |
In 1996, Ishihara et al. reported boronic acid-catalyzed dehydrative condensation between carboxylic acids and amines. Nevertheless, more excellent catalytic systems have been demanded for practical synthesis of amides and peptides. In this subject, we found that dehydrative condensation between carboxylic acids and amines more rapidly proceeded in the presence of catalytic amounts of boronic acid and N,N-dimethylaminopyridine N-oxide (DMAPO). After arboxylic acids were activated with boronic acids as mixed anhydrides, they were further activated with DMAPO as DMAPO esters. The latter intermediate was more active than the former one. Very interestingly, this new catalytic system, boronic acid/DMAPO, was effective for chemoselective amide condensation of conjugated carboxylic acids. In contrast, DMAP was much less effective than DMAPO.
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