Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β-Aminovinylphosphine Oxides

Hai Huang; Hongjun Zhu; Jun Yong Kang

doi:10.1021/acs.orglett.8b01065

Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β-Aminovinylphosphine Oxides

Hai Huang, Hongjun Zhu, Jun Yong Kang

化学与分子工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

29 引用（Scopus）

摘要

A metal-free hydrophosphorylation of ynamides with diaryl phosphine oxides has been developed. A highly E-selective and β-regioselective hydrophosphorylation protocol has been established as a general method for the synthesis of diversely hydrophosphinylated products employing an in situ generated electrophilic phosphorus species. Deuterium incorporation experiments suggest that the amino phosphirenium intermediate undergoes a concerted ring-opening hydrolysis upon treatment with H₂O to exclusively furnish β-aminovinylphosphine oxides.

源语言	英语
页（从-至）	2778-2781
页数	4
期刊	Organic Letters
卷	20
期	9
DOI	https://doi.org/10.1021/acs.orglett.8b01065
出版状态	已出版 - 4 5月 2018

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AB - A metal-free hydrophosphorylation of ynamides with diaryl phosphine oxides has been developed. A highly E-selective and β-regioselective hydrophosphorylation protocol has been established as a general method for the synthesis of diversely hydrophosphinylated products employing an in situ generated electrophilic phosphorus species. Deuterium incorporation experiments suggest that the amino phosphirenium intermediate undergoes a concerted ring-opening hydrolysis upon treatment with H2O to exclusively furnish β-aminovinylphosphine oxides.

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Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β-Aminovinylphosphine Oxides

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