Organic Chemistry Portal



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:

A. H. Abazid, T.-N. Hollwedel, B. J. Nachtsheim, Org. Lett., 2021, 23, 5076-5080.

DOI: 10.1021/acs.orglett.1c01607

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words

2-oxazolines, Selectfluor, hypervalent iodine compounds, organocatalysis

ID: J54-Y2021