Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes

Saima Tarannum, Sahid Sk, Subhomoy Das, Imtiyaz Ahmad Wani and Manas K. Ghorai*

*Department of Chemistry, Indian Institute of Technology, 208016 Kanpur, Uttar Pradesh, India, Email: mkghoraiiitk.ac.in

S. Tarannum, S. Sk, S. Das, I. A. Wani, M. K. Ghorai, J. Org. Chem., 2020, 85, 367-379.

DOI: 10.1021/acs.joc.9b02278

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Abstract

A mild one-pot synthesis of highly functionalized imidazolidines and oxazolidines via S_N2-type ring-opening of activated aziridines and epoxides with amines followed by p-toluenesulfonic acid catalyzed intramolecular cyclization with aldehydes tolerates a variety of functional groups and furnishes the desired products in high yields with excellent stereoselectivities.

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Key Words

Imidazolidines

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ID: J42-Y2020