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Regio‐ and Stereoselective Hydrophosphorylation of Ynamides: A Facile Approach to ( Z )‐ β ‐Phosphor‐Enamides
Author(s) -
Peng Zhiyuan,
Zhang Zhenming,
Zeng Xianzhu,
Tu Yongliang,
Zhao Junfeng
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900734
Subject(s) - phosphor , stereoselectivity , chemistry , diphenylphosphine oxide , isomerization , diphenylphosphine , combinatorial chemistry , substrate (aquarium) , phosphine oxide , phosphine , catalysis , medicinal chemistry , organic chemistry , optoelectronics , materials science , oceanography , geology
The first trans ‐selective β ‐hydrophosphorylation of ynamides, which provides a facile approach to ( Z )‐ β ‐phosphor‐enamide derivatives in moderate to excellent yields and with excellent regio‐ and stereoselectivity, is described. This transition‐metal‐free reaction is featured with operationally simple procedure, mild reaction conditions, readily available starting materials, broad substrate scope and good functional‐group tolerance. It is noted that the ( Z )‐ β ‐phosphor (V)‐enamides can be prepared from the oxidation of the corresponding phosphine derivatives or the direct β ‐hydrophosphorylation of ynamides with diphenylphosphine oxide. In addition, cis‐trans isomerization of ( Z )‐ β ‐phosphor (V)‐enamides can be easily realized to furnish the corresponding ( E )‐ β ‐phosphor (V)‐enamides. This advantageous feature enables the preparation of ( Z )‐ β ‐phosphor (V)‐enamides as well as ( E )‐ β ‐phosphor (V)‐enamides from the same starting materials.