Catalytic, Enantioselective Syn-Oxyamination of Alkenes

The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs and as chiral ligands. The reaction proceeds in good yields with excellent enantio- and diastereoselectivity for a variety of alkenes and pendant functional groups such as sulfonamides, alkyl halides, and glycol-protected ketones. Furthermore, the rapid generation of oxazoline products is demonstrated in the expeditious assembly of chiral PHOX ligands as well as diversely protected amino alcohols.

Automated summary

This study reports a method for the chemo-, regio-, diastereo-, and enantioselective oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst. The reaction demonstrates good yields and excellent enantio- and diastereoselectivity for a variety of alkenes and different functional groups. The use of N-tosylamides to generate oxazoline products allows for the assembly of chiral ligands and various protected amino alcohols in an expedited manner.