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Ring‐Opening of Carbamate‐Protected Aziridines and Azetidines in Liquid Sulfur Dioxide
Author(s) -
Lugiņina Jevgeņija,
Uzuleņa Jevgeņija,
Posevins Daniels,
Turks Māris
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600141
Subject(s) - chemistry , carbamate , ring (chemistry) , racemization , solvent , sulfur dioxide , organic chemistry , sulfur , stereocenter , halide , lewis acids and bases , polymer chemistry , catalysis , enantioselective synthesis
The reactions of halides or pseudohalides of group I and II metals with carbamate‐protected aziridines and azetidines in liquid sulfur dioxide as solvent resulted in the efficient ring‐opening of these heterocycles. Sulfur dioxide, as a highly polar solvent, solubilizes the inorganic salts and acts as a mild Lewis acid to accelerate the ring‐opening. For this reason, carbamate‐protected small heterocycles can be used instead of the corresponding sulfonamides, the activities of which are well‐established in ring‐opening reactions. Thiols also performed well in the SO 2 ‐assisted ring‐opening of aziridines. This procedure occurred without racemization of the stereogenic centers.