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作为氢占位基的环己 - 2,5 - 二烯基：乙醛替代物的有机催化迈克尔加成反应

The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate.

作者信息

Chen Weiqiang, Fang Huaquan, Xie Kaixue, Oestreich Martin

机构信息

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

出版信息

Chemistry. 2020 Nov 26;26(66):15126-15129. doi: 10.1002/chem.202003764. Epub 2020 Oct 22.

DOI:10.1002/chem.202003764
PMID:32808731
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7756304/
Abstract

An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi-Jørgensen catalyst and can be removed by a boron Lewis acid mediated C-C bond cleavage. The robust two-step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.

摘要

引入一种在α位带有环己-2,5-二烯基的醛作为高反应性乙醛的可储存替代物。环己-2,5-二烯基单元与林原-约根森催化剂促进的对硝基烯烃的对映选择性迈克尔加成反应兼容，并且可以通过硼路易斯酸介导的碳-碳键裂解去除。这种稳健的两步序列不需要直接使用乙醛时通常所需的大量过量醛组分。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/fdb69ffc0b08/CHEM-26-15126-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/721d87ee6379/CHEM-26-15126-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/9e424bea5766/CHEM-26-15126-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/fdb69ffc0b08/CHEM-26-15126-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/721d87ee6379/CHEM-26-15126-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/9e424bea5766/CHEM-26-15126-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad58/7756304/fdb69ffc0b08/CHEM-26-15126-g003.jpg

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