4.4 Article

The Design and Synthesis of Phenylcyclopropane-Based Secondary Amine Catalysts and Their Applications in Asymmetric Reactions

期刊

SYNLETT
卷 33, 期 18, 页码 1778-1787

出版社

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1796-7387

关键词

amine catalyst; cyclopropane; ketimine; asymmetric reaction; Mannich reaction; conjugate addition

资金

  1. Japan Society for the Promotion of Science (JSPS), KAKENHI [JP26220803, JP18H01975, JP20H04815, JP20H04828]

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A novel amine catalyst - phenylcyclopropane-based amine catalyst - has been designed, which possesses a similar chiral environment to that of binaphthyl-based amine catalysts and exhibits unique chemo- and stereoselectivity in several asymmetric reactions.
Most chiral secondary amine catalysts are usually synthesized from chiral amino acids and their derivatives. On the other hand, amine catalysts based on a binaphthyl backbone have previously been developed, and show unique chemo- and stereoselectivity in several asymmetric reactions. However, in spite of their utility, the applications of binaphthyl-based amines in asymmetric reactions are still rare due to their synthetic inefficiency. In this context, we have designed amine catalysts possessing a phenylcyclopropane scaffold as a novel chiral motif. These novel catalysts can be synthesized easily and construct a similar chiral environment to that of binaphthyl-based amine catalysts. In addition, a phenylcyclopropane-based amino sulfonamide is found to be an effective catalyst for syn-selective Mannich reactions and conjugate additions using alkynyl Z-ketimines.

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