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Carbonyl Imines from Oxaziridines: Generation and Cycloaddition of NOC Dipoles
Author(s) -
Partridge Katherine M.,
Guzei Ilia A.,
Yoon Tehshik P.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200905801
Subject(s) - cycloaddition , lewis acids and bases , chemistry , catalysis , oxazoline , 1,3 dipolar cycloaddition , scandium , sulfonyl , aziridine , imine , medicinal chemistry , organic chemistry , ring (chemistry) , alkyl
Dipoles apart : Unusual 1,3‐dipolar carbonyl imines are generated in the presence of a bulky scandium(III) catalyst by undergoing a Lewis acid catalyzed rearrangement of N ‐sulfonyl oxaziridines. The 1,3‐dipolar carbonyl imines then undergo subsequent cycloaddition with a variety of dipolarophiles. tmbox=2,2′‐isopropylidenebis(4,4‐dimethyl‐2‐oxazoline).