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

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2778-2781
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.8b01065
State	Published - 4 May 2018

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abstract = "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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AU - Zhu, Hongjun

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N2 - 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.

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

Abstract

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