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喹诺酮的高度对映选择性催化炔基化反应：底物范围、机理研究及其在合成手性杂环生物碱和二胺中的应用

Highly Enantioselective Catalytic Alkynylation of Quinolones: Substrate Scope, Mechanistic Studies, and Applications in the Syntheses of Chiral -Heterocyclic Alkaloids and Diamines.

作者信息

Guan Yong, Buivydas Tadas A, Lalisse Remy F, Laybourn Kalen B, Stern Charlotte, Richins Margaret, Burns Sean M, Shelby Arielle, Hadad Christopher M, Mattson Anita E

机构信息

Department of Chemistry and Biochemistry, Worcester Polytechnic Institute, 60 Prescott Street, Worcester, Massachusetts 01609, United States.

Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.

出版信息

ACS Catal. 2023 May 23;13(11):7661-7668. doi: 10.1021/acscatal.3c01536. eCollection 2023 Jun 2.

DOI:10.1021/acscatal.3c01536
PMID:37288090
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10243307/
Abstract

The alkynylation of 4-siloxyquinolinium triflates has been achieved under the influence of copper bis(oxazoline) catalysis. The identification of the optimal bis(oxazoline) ligand was informed through a computational approach that enabled the dihydroquinoline products to be produced with up to 96% enantiomeric excess. The conversions of the dihydroquinoline products to biologically relevant and diverse targets are reported.

摘要

在双（恶唑啉）铜催化作用下实现了4-硅氧基喹啉三氟甲磺酸盐的炔基化反应。通过计算方法确定了最佳双（恶唑啉）配体，该方法能够以高达96%的对映体过量生成二氢喹啉产物。本文报道了二氢喹啉产物向具有生物学相关性的多种目标产物的转化情况。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3fe/10243307/dfd06dcad748/cs3c01536_0012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3fe/10243307/dfd06dcad748/cs3c01536_0012.jpg

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Molecules. 2022 Feb 1;27(3):995. doi: 10.3390/molecules27030995.
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Cu(I)-Catalyzed Alkynylation of Quinolones.
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