Metal-Free Azidation of α-Hydroxy Esters and α-Hydroxy Ketones Using Azidotrimethylsilane
We herein report a commercially available perchloric acid catalyst capable of catalyzing the azidation of α-hydroxy esters, α-hydroxy ketones and taddols using azidotrimethylsilane in dichloromethane at room temperature. Various substituted tertiary alcoh
Yin, Xiao-Ping,Zhu, Lei,Zhou, Jian
supporting information
p. 1116 - 1122
(2018/01/27)
SN2 displacement at the quaternary carbon center: A novel entry to the synthesis of α,α-disubstituted α-amino acids This Letter is dedicated to the late Professor Harry Wasserman, a great chemist as well as a splendid artist
A novel method for the SN2 reaction on quaternary carbon atoms using bis(p-nitrophenyl)phosphorazidate has been developed. Chiral tertiary alcohols were directly converted into the corresponding chiral tertiary azides with complete inversion of configuration. Several α,α-disubstituted α-amino esters or amino acids were prepared through the conversion of azides to the corresponding amines by catalytic hydrogenation.