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; Manas K. Ghorai

doi:10.1021/acs.joc.9b02278

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, Manas K. Ghorai

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A mild one-pot stereospecific synthetic route to highly functionalized imidazolidines and oxazolidines via S_N2-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.

Original language	English
Pages (from-to)	367-379
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	85
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.9b02278
State	Published - 17 Jan 2020
Externally published	Yes

Bibliographical note

Funding 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.

Publisher Copyright:
Copyright © 2019 American Chemical Society.

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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.",

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AU - Wani, Imtiyaz Ahmad

AU - Ghorai, Manas K.

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

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