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（）-选择性魏因赖伯酰胺型霍纳-沃兹沃思-埃蒙斯反应：反应条件、底物范围、活性膦酰烯醇镁的分离及应用的影响

()-Selective Weinreb Amide-Type Horner-Wadsworth-Emmons Reaction: Effect of Reaction Conditions, Substrate Scope, Isolation of a Reactive Magnesium Phosphonoenolate, and Applications.

作者信息

Murata Takatsugu, Tsutsui Hisazumi, Shiina Isamu

机构信息

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

出版信息

J Org Chem. 2024 Nov 1;89(21):15414-15435. doi: 10.1021/acs.joc.4c01140. Epub 2024 Oct 11.

DOI:10.1021/acs.joc.4c01140
PMID:39393081
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11536377/
Abstract

An PrMgCl-deprotonating Weinreb amide-type Horner-Wadsworth-Emmons (HWE) reaction was developed, and the effects of diverse reaction conditions, including the base, cation, solvent, and concentration, were investigated to broaden the substrate scope and achieve high ()-selectivity. The Weinreb amide-type phosphonoenolate generated from PrMgCl was found to be isolable, stable for at least over a half year, and applicable in the HWE reaction keeping high productivity and selectivity compared with the in situ generated phosphonoenolate. The results prompted us to perform an application study including successive elongation, synthesis of a biscyclopropane, and Weinreb ketone syntheses.

摘要

开发了一种用PrMgCl去质子化的Weinreb酰胺型霍纳-沃兹沃思-埃蒙斯（HWE）反应，并研究了包括碱、阳离子、溶剂和浓度在内的各种反应条件的影响，以拓宽底物范围并实现高（）-选择性。发现由PrMgCl生成的Weinreb酰胺型膦烯醇化物是可分离的，至少可稳定半年以上，并且与原位生成的膦烯醇化物相比，可用于HWE反应并保持高生产率和选择性。这些结果促使我们进行了一项应用研究，包括连续延长、双环丙烷的合成以及Weinreb酮的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/cf4053b32770/jo4c01140_0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/9c0a19b5904a/jo4c01140_0006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/cdbebed5e475/jo4c01140_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/cf4053b32770/jo4c01140_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/dea5237ed6fa/jo4c01140_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/538a8c0a94bc/jo4c01140_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/4e5977bd5e67/jo4c01140_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/0507869d2c3c/jo4c01140_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/8338986cb081/jo4c01140_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/9c0a19b5904a/jo4c01140_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/e59ebbc3a642/jo4c01140_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/cdbebed5e475/jo4c01140_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b09/11536377/cf4053b32770/jo4c01140_0009.jpg

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()-Selective Weinreb Amide-Type Horner-Wadsworth-Emmons Reaction: Effect of Reaction Conditions, Substrate Scope, Isolation of a Reactive Magnesium Phosphonoenolate, and Applications.（）-选择性魏因赖伯酰胺型霍纳-沃兹沃思-埃蒙斯反应：反应条件、底物范围、活性膦酰烯醇镁的分离及应用的影响
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