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首页> 外文期刊>Chemistry: A European journal >Comparing the enantioselective power of steric and electrostatic effects in transition-metal-catalyzed asymmetric synthesis
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Comparing the enantioselective power of steric and electrostatic effects in transition-metal-catalyzed asymmetric synthesis

机译：比较过渡金属催化不对称合成中空间和静电效应的对映选择性

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The current approach to improve and tune the enantioselective performances of transition-metal catalysts for asymmetric synthesis is mostly focused to modifications of the steric properties of the ancillary ligands of the active metal. Nevertheless, it is also known that electrostatic effects can have a remarkable role to promote selectivity in asymmetric synthesis. Using the Rh-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone leading to chiral 3-phenylcyclohexanone as an example, we could show that high enantioselectivity can be indeed achieved using catalysts essentially based either on steric or electrostatic effects as the main source of enantioselective induction. In this contribution we suggest that the analysis of the surface of interaction between the catalyst and the substrate could be a useful tool to quantify the power of steric and electrostatic effects of catalysts. Steric versus electronic: Analysis of two prototype Rh catalysts show that high enantioselectivity in asymmetric synthesis can be achieved using either steric or electrostatic effects. Topographic maps of the interaction surface between the catalyst and the substrate are proposed as a tool to quantify these effects.
机译：当前改善和调节过渡金属催化剂用于不对称合成的对映选择性的方法主要集中在活性金属辅助配体的空间性质的改变上。然而，还已知静电效应可以在促进不对称合成中的选择性方面发挥显著作用。以Rh催化的苯基硼酸向2-环己烯酮的不对称1,4-加成反应生成手性3-苯基环己酮为例，我们可以证明，使用基本上基于空间或静电效应的催化剂，确实可以实现高对映选择性。对映选择性诱导的主要来源。在这一贡献中，我们建议对催化剂和底物之间相互作用表面的分析可能是量化催化剂的空间和静电作用能力的有用工具。立体与电子：两种原型Rh催化剂的分析表明，利用空间或静电效应均可实现不对称合成中的高对映选择性。提出了催化剂和底物之间相互作用表面的形貌图作为量化这些作用的工具。

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