Issue 16, 2016

Inherently chiral heterocyclic resorcinarenes using a Diels–Alder reaction

Abstract

This paper presents a novel approach to highly diastereoselective synthesis of resorcinarenes having enlarged cavities. Inherently chiral heterocyclic resorcinarenes have been obtained with unusually high diastereoselecivity by a “one pot” sequence involving thermal generation of o-quinomethide resorcinarene derivatives and the subsequent Diels–Alder reaction with dienophiles (exemplified by α-methylstyrene). The diastereoselectivity of this reaction is explained based on the thermodynamic stability of the products. The enantiomers of rac-4 have been separated by HPLC and their absolute configuration was assigned by comparison of their experimental and theoretical CD spectra.

Graphical abstract: Inherently chiral heterocyclic resorcinarenes using a Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
07 Dec 2015
Accepted
21 Jan 2016
First published
26 Jan 2016
This article is Open Access
Creative Commons BY license

RSC Adv., 2016,6, 13027-13031

Author version available

Inherently chiral heterocyclic resorcinarenes using a Diels–Alder reaction

W. Iwanek, K. Stefańska, A. Szumna and M. Wierzbicki, RSC Adv., 2016, 6, 13027 DOI: 10.1039/C5RA26106F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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