Carbonyl Imines from Oxaziridines: Generation and Cycloaddition of NOC Dipoles | Zendy

Partridge Katherine M. | Zendy; Guzei Ilia A. | Zendy; Yoon Tehshik P. | Zendy

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Carbonyl Imines from Oxaziridines: Generation and Cycloaddition of NOC 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).

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