Issue 31, 2017
From the journal:

Chemical Communications

Domino ring-opening cyclization (DROC) of activated aziridines and epoxides with nitrones via dual-catalysis “on water”†

Imtiyaz Ahmad Wani,a   Masthanvali Sayyada  and  Manas K. Ghorai ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India
E-mail: mkghorai@iitk.ac.in
Fax: +91-512-2596806
Tel: +91-512-2597518

Abstract

An efficient and green “on water” regio- and stereoselective synthetic route to chiral 1,2,4-oxadiazinanes and 1,4,2-dioxazinanes with excellent yields (up to 99%) and de/ee (>99%) has been developed for the first time via the domino ring-opening cyclization (DROC) of N-activated aziridines and epoxides with nitrones using LiClO4/Bu4NBF4 a dual catalyst system. The developed green strategy features a broader substrate scope and mild reaction conditions, and successfully overcomes the competitive oxidative ring opening of aziridines. Further synthetic significances of this green protocol are the formation of the products (i) as single diastereomers starting from a mixture of cis/trans disubstituted aziridines via dynamic kinetic epimerization (DKE) and (ii) via a multicomponent approach starting from N-methyl hydroxylamine hydrochloride, benzaldehyde and aziridine.

Graphical abstract: Domino ring-opening cyclization (DROC) of activated aziridines and epoxides with nitrones via dual-catalysis “on water”

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Article information

DOI
https://doi.org/10.1039/C7CC01033H
Article type
Communication
Submitted
09 Feb 2017
Accepted
26 Mar 2017
First published
28 Mar 2017

Chem. Commun., 2017,53, 4386-4389

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Domino ring-opening cyclization (DROC) of activated aziridines and epoxides with nitrones via dual-catalysis “on water”

I. A. Wani, M. Sayyad and M. K. Ghorai, Chem. Commun., 2017, 53, 4386 DOI: 10.1039/C7CC01033H

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