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Synlett 2022; 33(18): 1778-1787
DOI: 10.1055/a-1796-7387
DOI: 10.1055/a-1796-7387
cluster
Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis
The Design and Synthesis of Phenylcyclopropane-Based Secondary Amine Catalysts and Their Applications in Asymmetric Reactions
This work was supported by the Japan Society for the Promotion of Science (JSPS), KAKENHI (Grant Nos. JP26220803, JP18H01975, JP20H04815 and JP20H04828 in Hybrid Catalysis).
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 additionPublication History
Received: 02 February 2022
Accepted after revision: 13 March 2022
Accepted Manuscript online:
13 March 2022
Article published online:
13 April 2022
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For representative amine-catalyzed asymmetric reactions using ketimines, see:
For reviews, see: