Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive Gem-Cyanation-Phosphonylation of Secondary Amides.

Org Lett

Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering , Xiamen University, Xiamen 361005 , Fujian , China.

Published: May 2019

A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a TfO-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol can be run on a gram scale.

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http://dx.doi.org/10.1021/acs.orglett.9b01257DOI Listing

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