Issue 47, 2012
From the journal:

Organic & Biomolecular Chemistry

A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates – unexpected formation of δ-spirolactones†

Christian Hempel,a   Nicole M. Weckenmann,a   C. Maichle-Moessmerb  and  Boris J. Nachtsheim*a  

* Corresponding authors

a Eberhard Karls University, Institute of Organic Chemistry, Auf der Morgenstelle 18, Tuebingen, Germany
E-mail: boris.nachtsheim@uni-tuebingen.de
Fax: +49 7071 29-5897
Tel: +49 7071 29-72035

b Eberhard Karls University, Institute of Inorganic Chemistry, Auf der Morgenstelle 18, Tuebingen, Germany

Abstract

On the way towards a new total synthesis of (S)-arogenate, a novel aryl-λ3-iodane-mediated oxidative spirocyclization of para-substituted phenol derivatives has been discovered. Starting from easy accessible 2-(4-hydroxybenzamido)acrylates we could construct spirocyclic lactams in up to 52% yield. Under alternative reaction conditions the same precursors underwent an unexpected oxidative spirocyclization yielding a novel δ-spirolactone in up to 70% yield.

Graphical abstract: A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates – unexpected formation of δ-spirolactones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB26815A
Article type
Communication
Submitted
16 Sep 2012
Accepted
19 Oct 2012
First published
22 Oct 2012

Org. Biomol. Chem., 2012,10, 9325-9329

Permissions

Request permissions

A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates – unexpected formation of δ-spirolactones

C. Hempel, N. M. Weckenmann, C. Maichle-Moessmer and B. J. Nachtsheim, Org. Biomol. Chem., 2012, 10, 9325 DOI: 10.1039/C2OB26815A

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