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Catalyst‐Free Regio‐ and Stereospecific Synthesis of β‐Sulfonamido Dithiocarbamates: Efficient Ring‐Opening Reactions of N ‐Tosyl Aziridines by Dialkyldithiocarbamates
Author(s) -
Alagiri Kaliyamoorthy,
Prabhu Kandikere Ramaiah
Publication year - 2011
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.201100817
Subject(s) - stereospecificity , aziridine , ring (chemistry) , chemistry , alkyl , tosyl , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry
Lord of the ring‐opening! A metal‐free strategy involving ring‐opening of aziridines by the sodium salt of dialkyldithiocarbamate has been employed to give a variety of β‐sulfonamido dithiocarbamates. The in situ generation of dialkyldithiocarbamates provided a simple, user‐friendly, one‐pot reaction that gives aziridine ring‐opened products (see scheme; Ts=tosyl; R=alkyl; R 1 , R 2 =alkyl, cycloalkyl).