Grant-in-Aid for Specially Promoted Research: Design of High-Performance Organocatalysts for the Application to Fine Organic Synthesis SitemapJapanese
  • Maruoka Group, Department of Chemistry, Graduate School of Science, Kyoto University
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Research [Bifunctional Organocatalyst]

 During the last eleven years, gold rush of organocatalysis has come, and proline and its derivatives as bifunctional organocatalysts have been undoubtedly centered on the development of organocatalyzed reactions. On the other hand, our group developed axially chiral secondary amine catalysts as artificially designed bifunctional organocatalysts (Scheme 1). These catalysts have shown unique reactivity and selectivity in comparison with proline and its derivatives, and many characteristic features of these catalysts have been reported. The representative feature of a designer axially chiral bifunctional organocatalyst in the Mannich reaction was shown in Scheme 1. In contrast to the syn-selective Mannich reaction catalyzed by proline, the reaction using axially chiral amino sulfonamide (S)-2 achieves anti-selective Mannich reaction with high enantioselectivity.

Scheme 1

 Different types of bifunctional organocatalysts 35 have also been developed for the highly enantioselective reactions (Schemes 2 and 3).

Scheme 2

Scheme 3