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对映异构的2-(喹啉-8-基)苯甲醇的化学酶法动态动力学拆分

Chemoenzymatic Dynamic Kinetic Resolution of Atropoisomeric 2-(Quinolin-8-yl)benzylalcohols.

作者信息

Coto-Cid Juan M, Hornillos Valentín, Fernández Rosario, Lassaletta José M, de Gonzalo Gonzalo

机构信息

Facultad de Química, Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/Prof. García González, 1, 41012 Sevilla, Spain.

Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Avda. Américo Vespucio, 49, 41092 Sevilla, Spain.

出版信息

J Org Chem. 2025 Apr 18;90(15):5120-5124. doi: 10.1021/acs.joc.4c02996. Epub 2025 Apr 9.

DOI:10.1021/acs.joc.4c02996
PMID:40203203
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12160057/
Abstract

The chemoenzymatic dynamic kinetic resolution of 2-(quinolin-8-yl)benzylalcohols using a combination of lipases and ruthenium catalysts is described. While CalB lipase performs highly selective enzymatic kinetic resolution, the combination with Shvo's or Bäckvall's catalysts promotes atropisomerization of the substrate via the reversible formation of configurationally labile aldehydes, thereby enabling a dynamic kinetic resolution. This synergistic approach was applied to the synthesis of a variety of heterobiaryl acetates in excellent yields and enantioselectivities.

摘要

描述了使用脂肪酶和钌催化剂的组合对2-(喹啉-8-基)苄醇进行化学酶促动态动力学拆分。虽然CalB脂肪酶具有高度选择性的酶促动力学拆分作用，但与Shvo或Bäckvall催化剂组合可通过构型不稳定醛的可逆形成促进底物的阻转异构化，从而实现动态动力学拆分。这种协同方法被应用于以优异的产率和对映选择性合成多种杂芳基乙酸酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/923edf5d90b2/jo4c02996_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/ff966fdd2d1a/jo4c02996_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/9666b2acf608/jo4c02996_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/ddf1c6b6f5b0/jo4c02996_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/923edf5d90b2/jo4c02996_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/ff966fdd2d1a/jo4c02996_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/9666b2acf608/jo4c02996_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/ddf1c6b6f5b0/jo4c02996_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aea2/12160057/923edf5d90b2/jo4c02996_0004.jpg

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Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction.
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Stereodynamic Strategies to Induce and Enrich Chirality of Atropisomers at a Late Stage.后期诱导和富集阻转异构体手性的立体动力学策略。
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