Catalytic Asymmetric Synthesis. Группа авторов
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3 ASYMMETRIC BASE ORGANOCATALYSIS
Azusa Kondoh and Masahiro Terada
Graduate School of Science, Tohoku University, Sendai, Japan
3.1. INTRODUCTION
Brønsted base catalysis – the catalysis by a small molecule having Brønsted basicity, such as an amine – is one of the most fundamental types of catalysis in organic chemistry. The catalysis enables the direct transformation of starting compounds into desired products in a highly atom‐economical fashion under mild reaction conditions and, thus, has been widely utilized in organic synthesis over a long period of time. In particular, the catalysis has recently attracted considerable attention as a family of “environmentally benign” organocatalysis, and the development of enantioselective reactions has been intensively explored by using chiral uncharged organobases as a catalyst [1]. Generally, the catalysis is initiated by the generation of an anionic nucleophile through the direct deprotonation of a pronucleophile by a Brønsted base catalyst (Figure 3.1). Then, the transformation of the anionic nucleophile, such as addition to an unsaturated bond, rearrangement, and isomerization, proceeds to generate a different anionic intermediate. Finally, the protonation of the resulting anionic intermediate with the conjugate acid of the Brønsted base catalyst (or the other molecule of a pronucleophile in some cases) occurs to provide the desired products along with the regeneration of the catalyst (or the anionic nucleophile), completing the catalytic cycle. In the case of enantioselective reactions, the transformation of the anionic nucleophile (and/or the protonation of the anionic intermediate) proceeds in a stereoselective fashion under the influence of the conjugate acid of a chiral Brønsted base catalyst, and an enantio‐enriched product can be obtained.
In