Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxaz(ol)ines
Ayham H. Abazid, Tom-Niklas Hollwedel and Boris J. Nachtsheim*
*University of Bremen, Institute of Organic and Analytical Chemistry, Leobener Straße 7, 28359 Bremen, Germany,
Email: nachtsheim
uni-bremen.de
A. H. Abazid, T.-N. Hollwedel, B. J. Nachtsheim, Org. Lett., 2021, 23, 5076-5080.
DOI: 10.1021/acs.orglett.1c01607
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Abstract
A chiral triazole-substituted iodoarene catalyzes an enantioselective oxidative cyclization of N-allyl carboxamides to provide highly enantioenriched oxazolines and oxazines. Quaternary stereocenters can be constructed and, besides N-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates.
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proposed mechanism
Key Words
2-oxazolines, Selectfluor, hypervalent iodine compounds, organocatalysis
ID: J54-Y2021
