对映选择性Brønsted酸催化的新进展:手性离子对催化及其他。

M Rueping, E Sugiono
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摘要

设计具有高对映体选择性的催化反应是有机合成的一个重要目标。对这一研究领域的兴趣日益增加,特别是在金属催化转化领域取得了实质性进展。近年来,有机小分子已被用作各种对映选择性反应的有机催化剂。其中,仲胺催化剂应用最为广泛,可以通过形成烯胺(烯胺催化)激活亲核组分,也可以通过形成最小中间体激活亲电试剂(胺催化)。此外,手性二醇和硫脲,以及碳和dmap衍生物(氢键-亲核催化),已被证明是对映选择性转化的多功能催化剂。另一种方法是使用手性溴离子酸激活亲电试剂或亲核试剂。与氨基、羰基、吡啶和氢键催化的转化相比,对映选择性Brønsted酸催化是最近才出现的重要和有前途的研究领域。在过去两年的研究过程中,我们在对映选择性Brønsted酸催化领域做出了重大贡献,并首次证明了手性Brønsted酸催化剂在各种对映选择性转化中可以提供比金属催化过程更好或至少相当的结果。在本章中,我们将重点介绍我们的一些最新成果,并将描述我们如何最初进入不对称Brønsted酸催化领域,从仿生方法开始,以自然为榜样。
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New developments in enantioselective Brønsted acid catalysis: chiral ion pair catalysis and beyond.

The design of catalytic reactions that proceed with high enantioselectivity is an important goal in organic synthesis. Increased interest in this research area has resulted in substantial progress, particularly in the field of metal catalyzed transformations. In recent years small organic molecules have been used as organocatalysts for a variety of enantioselective reactions. Among these, secondary amine catalysts are the most widely applied and can be used in the activation of the nucleophilic component through enamine formation (enamine catalysis), or by formation of an iminum intermediate to activate the electrophile (iminium catalysis). Additionally, chiral diols and thioureas, as well as carbene- and DMAP-derivatives (hydrogen bonding-, nucleophilic catalysis), have been shown to be versatile catalysts for enantioselective transformations. An alternative to these strategies is the activation of an electrophile or nucleophile by use of a chiral Brønsted acid. Compared to amino-, carbene-, pyridine- and hydrogen-bonding catalyzed transformations, enantioselective Brønsted acid catalysis has only recently emerged as important and promising area of research. In the course of our research program we were able to contribute significantly to the field of enantioselective Brønsted acid catalysis over the last 2 years, and could demonstrate for the first time that in various enantioselective transformations chiral Brønsted acid catalysts can give better or at least comparable results to metal-catalyzed processes. In this chapter we will highlight some of our most recent results and will, additionally, describe how we initially entered the field of asymmetric Brønsted acid catalysis by starting of from a biomimetic approach using nature as a role model.

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