Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β‑Aminovinylphosphine Oxides
Document Type
Article
Publication Date
4-24-2018
Publication Title
Organic Letters
Volume
20
First page number:
2778
Last page number:
2781
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.
Disciplines
Chemistry
Language
English
Repository Citation
Huang, H.,
Zhu, H.,
Kang, J. Y.
(2018).
Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β‑Aminovinylphosphine Oxides.
Organic Letters, 20
2778-2781.
http://dx.doi.org/10.1021/acs.orglett.8b01065