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过渡金属催化的手性瞬态导向基团策略的对映选择性 C-H 官能化。

Transition Metal-Catalyzed Enantioselective C-H Functionalization via Chiral Transient Directing Group Strategies.

机构信息

Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.

出版信息

Angew Chem Int Ed Engl. 2020 Nov 2;59(45):19773-19786. doi: 10.1002/anie.202008437. Epub 2020 Aug 25.

DOI:10.1002/anie.202008437
PMID:32687690
Abstract

Transition metal-catalyzed enantioselective functionalization of C-H bond, the most abundant functionality in organic molecules, has emerged as an expedient synthetic approach to streamline the synthesis of complex chiral molecules. Despite significant progress, traditional directing group-enabled strategies require additional steps for the installation and removal of directing groups from the target molecule. The recently developed asymmetric C-H functionalization using chiral transient directing groups (cTDGs) offers a promising alternative that can circumvent this obstacle and therefore simplify the process. In this Minireview, we briefly discuss the advent and recent advances of this emerging concept, with an emphasis on discussing the creation of various stereogenic centers and the developments of cTDGs. Applications in natural product synthesis and ligand derivatizations are also discussed. We hope this Minireview will highlight the great potential of this strategy and help to inspire further endeavors.

摘要

过渡金属催化的 C-H 键手性功能化,作为一种有效的合成方法,已经广泛应用于复杂手性分子的合成中,C-H 键是有机分子中最丰富的功能基团。尽管已经取得了显著的进展,但传统的导向基团辅助策略需要额外的步骤来安装和去除目标分子中的导向基团。最近发展起来的使用手性瞬变导向基团(cTDG)的不对称 C-H 功能化提供了一种很有前途的替代方法,可以避免这一障碍,从而简化这一过程。在这篇综述中,我们简要讨论了这一新兴概念的出现和最新进展,重点讨论了各种立体中心的构建和 cTDG 的发展。还讨论了该策略在天然产物合成和配体衍生化方面的应用。我们希望这篇综述能够突出这一策略的巨大潜力,并有助于激发进一步的研究。

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