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手性镍催化非环酮的反芳基金属化环化反应。

Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones.

机构信息

The GlaxoSmithKline Carbon Neutral Laboratories for, Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU, UK.

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

出版信息

Chemistry. 2021 Apr 1;27(19):5897-5900. doi: 10.1002/chem.202100143. Epub 2021 Mar 5.

DOI:10.1002/chem.202100143
PMID:33533065
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8048927/
Abstract

Domino reactions involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary-alcohol-containing products in high enantioselectivities, are described. The reversible E/Z isomerization of the alkenylnickel intermediates enables overall anti-arylmetallative cyclization to occur. The ring system of the products are substructures of certain diarylindolizidine alkaloids.

摘要

描述了涉及（杂）芳基硼酸与炔烃的镍催化加成的多米诺反应，然后将烯基镍中间体环化到连接的无环酮上，以高对映选择性得到含有手性叔醇的产物。烯基镍中间体的可逆 E/Z 异构化使总体上发生反芳基金属化环化。产物的环系是某些二芳基吲哚里西丁生物碱的亚结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/0149f5db3d9d/CHEM-27-5897-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9975cf5d3252/CHEM-27-5897-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/91f0d3c1a3a1/CHEM-27-5897-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9530d28f4ec2/CHEM-27-5897-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9120ef7d7144/CHEM-27-5897-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/f48803db88bd/CHEM-27-5897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/0149f5db3d9d/CHEM-27-5897-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9975cf5d3252/CHEM-27-5897-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/91f0d3c1a3a1/CHEM-27-5897-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9530d28f4ec2/CHEM-27-5897-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/9120ef7d7144/CHEM-27-5897-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/f48803db88bd/CHEM-27-5897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2678/8048927/0149f5db3d9d/CHEM-27-5897-g003.jpg

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Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration.通过1,4-铑（I）迁移实现炔基1,3-二酮的催化对映选择性芳基化环化反应。
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