Phosphorodiamidic acid as a novel structural motif of brønsted acid catalysts for direct mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds

Phosphorodiamidic acid as a novel structural motif of brønsted acid catalysts for direct mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds
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DOI:
10.1055/s-2005-922783
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发表时间:
2006
期刊:
影响因子:
2
通讯作者:
M. Terada;K. Sorimachi;D. Uraguchi
M. Terada;K. Sorimachi;D. Uraguchi
中科院分区:
化学4区
文献类型:
--
作者:
M. Terada;K. Sorimachi;D. Uraguchi

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Phosphorodiamidic acid 1 was developed as an efficient Bronsted acid catalyst for the direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds. Phosphorodiamidic acids were proposed as a novel structural motif of enantioselective ­Bronsted acid catalysts because they possess unique features, including the capability of introducing various substituents to the nitrogen atoms and the preparation from readily available chiral diamines in a short step. We demonstrated that chiral phosphorodiamidic acid 1b derived from binaphthalene bis(sulfonamide) functioned as an enantioselective catalyst to give the Mannich product in an optically active form.