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LiAlH 4 ‐Induced Thia‐Aza‐Payne Rearrangement of Functionalized 2‐(Thiocyanatomethyl)aziridines into 2‐(Aminomethyl)thiiranes as an Entry to 5‐(Chloromethyl)thiazolidin‐2‐ones
Author(s) -
Dolfen Jeroen,
Van Hecke Kristof,
D'hooghe Matthias
Publication year - 2017
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.201700549
Subject(s) - chemistry , aziridine , moiety , intramolecular force , triphosgene , ring (chemistry) , medicinal chemistry , hydride , combinatorial chemistry , stereochemistry , organic chemistry , phosgene , hydrogen
Nonactivated 2‐(thiocyanatomethyl)aziridines with diverse substitution patterns were deployed as substrates to effect a LiAlH 4 ‐promoted thia‐aza‐Payne rearrangement to provide access to functionalized 2‐(aminomethyl)thiiranes in good to excellent yields (78–94 %). The developed strategy involved hydride reduction of the thiocyanato moiety followed by intramolecular aziridine ring opening. Subsequent exposure of the obtained 2‐(aminomethyl)episulfide intermediates to triphosgene resulted in the formation of 5‐(chloromethyl)thiazolidin‐2‐ones.