Issue 8, 2014
From the journal:

RSC Advances

Stereoselective domino azidation and [3 + 2] cycloaddition: a facile route to chiral heterocyclic scaffolds from carbohydrate derived synthons†

Debleena Bhattacharya,a   Abhijit Ghorai,a   Uttam Pal,b   Nakul Chandra Maitib  and  Partha Chattopadhyay*a  

* Corresponding authors

a Chemistry Division, CSIR-Indian Institute of Chemical Biology, Kolkata-700032, India
E-mail: partha@iicb.res.in
Fax: +91-33-24735197

b Structural Biology & Bioinformatics Division, CSIR-Indian Institute of Chemical Biology, Kolkata-700032, India

Abstract

A rapid one pot intermolecular aryl azidation and intramolecular azide-olefin cycloaddition protocol has been designed using carbohydrate precursors to generate optically active, aziridine fused oxa–aza heterocycles, related to DNA targeting anti-tumour agents which on further functionalization stereoselectively produce eight membered heterocyclic scaffolds. The structural conclusions were fully supported by a molecular modelling study based on density functional theory.

Graphical abstract: Stereoselective domino azidation and [3 + 2] cycloaddition: a facile route to chiral heterocyclic scaffolds from carbohydrate derived synthons

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3RA45363D
Article type
Paper
Submitted
26 Sep 2013
Accepted
07 Nov 2013
First published
20 Dec 2013

RSC Adv., 2014,4, 4155-4162

Permissions

Request permissions

Stereoselective domino azidation and [3 + 2] cycloaddition: a facile route to chiral heterocyclic scaffolds from carbohydrate derived synthons

D. Bhattacharya, A. Ghorai, U. Pal, N. Chandra Maiti and P. Chattopadhyay, RSC Adv., 2014, 4, 4155 DOI: 10.1039/C3RA45363D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements