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使用改良的斯蒂尔-根纳里型试剂进行高选择性霍纳-沃思瓦尔德-埃蒙斯(Horner-Wadsworth-Emmons)烯烃化反应。

Highly -Selective Horner-Wadsworth-Emmons Olefination Using Modified Still-Gennari-Type Reagents.

机构信息

Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.

出版信息

Molecules. 2022 Oct 21;27(20):7138. doi: 10.3390/molecules27207138.

Abstract

In this report, new, easily accessible reagents for highly -selective HWE reactions are presented. Alkyl di-(1,1,1,3,3,3-hexafluoroisopropyl)phosphonoacetates, structurally similar to Still-Gennari type reagents, were tested in HWE reactions with a series of various aldehydes. Very good -selectivity (up to a 98:2 : ratio) was achieved in most cases along with high yields. Application of the new reagents may be a valuable, practical alternative to the well-established Still-Gennari or Ando -selective carbonyl group olefination protocols.

摘要

在本报告中,我们提出了一些新的、易于获得的试剂,用于高度选择性的 HWE 反应。结构上类似于斯蒂尔-根纳里型试剂的烷基二-(1,1,1,3,3,3-六氟异丙基)膦酸酯,在与一系列不同醛的 HWE 反应中进行了测试。在大多数情况下,都实现了非常好的选择性(高达 98:2 的比例)和高收率。这些新型试剂的应用可能是对成熟的斯蒂尔-根纳里或安多选择性羰基烯烃化方案的一种有价值的、实用的替代方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f8ac/9609750/ebb1b995088a/molecules-27-07138-sch001.jpg

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