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Metal‐Free Azidation of α‐Hydroxy Esters and α‐Hydroxy Ketones Using Azidotrimethylsilane
Author(s) -
Yin XiaoPing,
Zhu Lei,
Zhou Jian
Publication year - 2018
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.201701345
Subject(s) - chemistry , perchloric acid , dichloromethane , catalysis , organic chemistry , reaction conditions , combinatorial chemistry , metal , compatibility (geochemistry) , chemical engineering , solvent , engineering
Abstract 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 alcohols are well tolerated in this reaction. C α ‐tetrasubstituted α‐amino acid derivatives were prepared by one‐pot sequential azidation and hydrogenation procedure. The advantage of this newly developed method includes operational simplicity, ready availability of catalyst, scale‐up ability, and also good functional group compatibility.