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通过对映选择性、铜氢催化的硅氧键与硅烷的偶联实现联萘酚和联苯酚的动力学拆分

Kinetic Resolution of BINOLs and Biphenols by Atroposelective, Cu-H-Catalyzed Si-O Coupling with Hydrosilanes.

作者信息

Böser Lisa A, Oestreich Martin

机构信息

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany.

出版信息

Org Lett. 2024 Nov 8;26(44):9531-9535. doi: 10.1021/acs.orglett.4c03557. Epub 2024 Oct 24.

DOI:10.1021/acs.orglett.4c03557
PMID:39448059
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11555675/
Abstract

A nonenzymatic kinetic resolution of monoprotected BINOL and biphenol derivatives by atroposelective Si-O coupling with hydrosilanes is described. The reaction relies on a previously unprecedented Cu-H-catalyzed silylation of phenols. The catalyst system consisting of CuCl, (,)-Ph-BPE, and NaOBu enables the enantioselective coupling of the phenolic hydroxy group with a hydrosilane with moderate to good selectivity factors.

摘要

本文描述了通过与硅烷进行阻转选择性Si-O偶联对单保护的联萘酚和联苯酚衍生物进行非酶动力学拆分。该反应依赖于一种前所未有的铜氢催化的酚类硅烷化反应。由氯化铜、（，）-Ph-BPE和丁醇钠组成的催化剂体系能够使酚羟基与硅烷进行对映选择性偶联，选择性因子适中至良好。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/9a8109ca8fa5/ol4c03557_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/f0ac235cd1cd/ol4c03557_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/d91c036e4318/ol4c03557_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/9a8109ca8fa5/ol4c03557_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/f0ac235cd1cd/ol4c03557_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/d91c036e4318/ol4c03557_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2daf/11555675/9a8109ca8fa5/ol4c03557_0003.jpg

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Enantiodivergent Kinetic Resolution of 1,1'-Biaryl-2,2'-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton-Todd Reaction.受 Atherton-Todd 反应启发的二肽-膦盐催化的 1,1'-联芳基-2,2'-二醇和氨基醇的对映体选择性动力学拆分。
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6
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