期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 347, 期 11-13, 页码 1595-1604出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505190
关键词
asymmetric synthesis; imines; Mannich reaction; organocatalysis; proline
In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.
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