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在环己烯核苷合成中的立体协同 Tsuji-Trost 反应。

A Stereoconvergent Tsuji-Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides.

机构信息

Department of Chemical Sciences, Università degli Studi di Napoli Federico II, via Cintia, 80126, Napoli, Italy.

出版信息

Chemistry. 2020 Feb 26;26(12):2597-2601. doi: 10.1002/chem.201905367. Epub 2020 Feb 11.

DOI:10.1002/chem.201905367
PMID:31860145
Abstract

A highly regio- and stereoselective route to d- and l-cyclohexenyl nucleosides has been devised, using the Tsuji-Trost reaction as the key step. Contrarily to the widely accepted mechanism (involving a net retention of configuration), the reaction proceeded in a highly stereoconvergent manner, providing cis nucleosides regardless of the relative configuration of the starting materials. DFT calculations confirmed the experimental data while suggesting the origin of the stereochemical reaction outcome.

摘要

已经设计出一种高区域和立体选择性的方法来合成 d-和 l-环己烯核苷，该方法使用 Tsuji-Trost 反应作为关键步骤。与广泛接受的机制（涉及构型的净保留）相反，该反应以高度立体转化的方式进行，无论起始原料的相对构型如何，都提供顺式核苷。DFT 计算证实了实验数据，同时提出了立体化学反应结果的起源。

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