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Amine‐Free Approach toward N ‐Toluenesulfonyl Amidine Construction: A Phosphite‐Mediated Beckmann‐Like Coupling of Oximes and p ‐Toluenesulfonyl Azide
Author(s) -
Fleury Lauren M.,
Wilson Erin E.,
Vogt Monika,
Fan Tiffany J.,
Oliver Allen G.,
Ashfeld Brandon L.
Publication year - 2013
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.201305141
Subject(s) - amidine , beckmann rearrangement , chemistry , azide , sulfonyl , enamine , bioorthogonal chemistry , amine gas treating , combinatorial chemistry , medicinal chemistry , catalysis , oxime , organic chemistry , click chemistry , alkyl
Atom hopping : A chlorophosphite‐mediated Beckmann ligation of oximes and p ‐toluenesulfonyl azide gives access to N ‐sulfonyl phosphoramidines in good to excellent yields. The reaction proceeds under exceptionally mild conditions and constitutes a bioorthogonal approach toward amidines by avoiding the use of amines and transition‐metal catalysts. dmp‐ol=3,3‐dimethylpropanediol.
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