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The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines
Author(s) -
Stanetty Christian,
Blaukopf Markus K.,
Lachmann Bodo,
Noe Christian R.
Publication year - 2011
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.201100358
Subject(s) - regioselectivity , aziridine , chemistry , racemization , cleavage (geology) , catalysis , alcohol , ring (chemistry) , medicinal chemistry , enantioselective synthesis , organic chemistry , stereochemistry , geotechnical engineering , fracture (geology) , engineering
Abstract The N ‐2,4‐dinitrophenylsulfonyl group (dinosyl, DNs) was found to be an excellent choice for the N‐activation of aziridines towards ring cleavage with primary, secondary, andsterically demanding tertiary alcohols. Alcoholysis does not need any additional catalyst and is regioselective for the less‐hindered position. No racemization in the aziridine formation or cleavage step was observed, and the resulting DNs‐sulfonamides can be deprotected quantitatively under mild conditions.