A mild one-pot stereospecific synthetic route to highly functionalized imidazolidines and oxazolidines via SN2-type ring-opening of the corresponding activated aziridines and epoxides with amines followed by p-toluenesulfonic acid (PTSA)-catalyzed intramolecular cyclization with aldehydes has been developed. The methodology tolerates a variety of functional groups and furnishes the desired products in high yields (up to 92%) with excellent stereoselectivities (de, ee > 99%). Interestingly, imidazolidines were formed as the cis-isomers, whereas oxazolidines were produced as trans-isomers exclusively.
|Number of pages||13|
|Journal||Journal of Organic Chemistry|
|State||Published - 17 Jan 2020|
Bibliographical noteFunding Information:
M.K.G. is grateful to IIT-Kanpur and DST, India, for financial support. S.T. thanks SERB, India, for National Post-Doctoral Fellowship, and S.S. thanks IIT-Kanpur for a Senior Research Fellowship.
Copyright © 2019 American Chemical Society.