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首页> 外文期刊>Chemistry: A European journal >Formation of Contiguous Quaternary and Tertiary Stereocenters by Sequential Asymmetric Conjugate Addition of Grignard Reagents to 2-Substituted Enones and Mg-Enolate Trapping
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Formation of Contiguous Quaternary and Tertiary Stereocenters by Sequential Asymmetric Conjugate Addition of Grignard Reagents to 2-Substituted Enones and Mg-Enolate Trapping

机译：格氏试剂对2-取代的烯酮的连续不对称共轭加成和镁-乙醇酸盐的捕获形成连续的第四级和第三级立体中心

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Herein a comprehensive study is provided on the asymmetric conjugate addition (ACA) of Grignard reagents to -substituted cyclic enones. After the elucidation of the optimal experimental conditions, the scope of Grignard reagents and Michael acceptors was examined. Whereas secondary Grignards gave better enantioselectivities with 2-cyclopentenones, both linear and branched Grignard reagents were tolerated for the ACA to 2-methylcyclohexenone. The sequential ACA-enolate trapping, which leads to quaternary stereocenters, was then studied. Thus, many electrophiles have been tested, thereby giving rise to highly functionalized cyclic ketones with contiguous -quaternary and -tertiary centers. The present technique is believed to bring a new approach to versatile terpenoid-like skeletons of bioactive natural products. Straightforward derivatizations of enantioenriched saturated cyclic ketones further support the potential of the present methodology in synthesis.
机译：本文提供了关于格氏试剂对取代的环烯酮的不对称共轭加成（ACA）的全面研究。在阐明最佳实验条件后，检查了格氏试剂和迈克尔受体的范围。二次格氏试剂对2-环戊烯酮的对映选择性更好，而线性和支化格氏试剂对ACA耐受2-甲基环己烯酮。然后研究了导致四元立体中心的连续ACA-烯醇化陷阱。因此，已经测试了许多亲电试剂，从而产生了具有连续的四级和三级中心的高度官能化的环酮。据信，本技术为生物活性天然产物的多用途类萜骨架提供了新方法。对映体富集的饱和环状酮的直接衍生化进一步支持了本方法在合成中的潜力。

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