Tarannum, Saima ; Sk, Sahid ; Das, Subhomoy ; Wani, Imtiyaz Ahmad ; Ghorai, Manas K. (2020) Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes The Journal of Organic Chemistry, 85 (2). pp. 367-379. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.9b02278
Related URL: http://dx.doi.org/10.1021/acs.joc.9b02278
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117080 |
| Deposited On: | 15 Apr 2021 07:41 |
| Last Modified: | 15 Apr 2021 07:41 |
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