Abstract
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.
1 Introduction
2 Design and Synthesis of Novel Chiral Secondary Amine Catalysts
3 Performance Evaluation of Phenylcyclopropane-Based Amine Catalysts
4 Development of Asymmetric Reactions Catalyzed by a Novel Chiral Amino Sulfonamide
5 Conclusions
Key words
amine catalyst - cyclopropane - ketimine - asymmetric reaction - Mannich reaction
- conjugate addition
