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One‐Pot Synthesis of O ‐Allylhydroxylamines through the Organocatalytic Oxidation of Tertiary Allylic Amines Followed by a [2,3]‐Meisenheimer Rearrangement
Author(s) -
Theodorou Alexis,
Limnios Dimitris,
Kokotos Christoforos G.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406173
Subject(s) - allylic rearrangement , chemistry , amine gas treating , organic chemistry , combinatorial chemistry , catalysis , medicinal chemistry
A cheap, green, and highly efficient one‐pot method for the synthesis of O‐protected allylic alcohols is described. By utilizing 2,2,2‐trifluoroacetophenone as the organocatalyst and H 2 O 2 as the oxidant, a variety of allylic amine N ‐oxides were synthesized, which upon heating are converted to the final products through a [2,3]‐Meisenheimer rearrangement.