Issue 86, 2013
From the journal:

Chemical Communications

Gated access to α-lithiated phenyltetrahydrofuran: functionalisation via direct lithiation of the parent oxygen heterocycle†‡

Rosmara Mansueto,a   Valentina Mallardo,a   Filippo Maria Perna,a   Antonio Salomonea  and  Vito Capriati*a  

* Corresponding authors

a Dipartimento di Farmacia – Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S, via E. Orabona 4, I-70125 Bari, Italy
E-mail: vito.capriati@uniba.it
Fax: +39 080 5442539
Tel: +39 080 5442174

Abstract

Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at −78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones.

Graphical abstract: Gated access to α-lithiated phenyltetrahydrofuran: functionalisation via direct lithiation of the parent oxygen heterocycle

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3CC45499A
Article type
Communication
Submitted
19 Jul 2013
Accepted
02 Sep 2013
First published
02 Sep 2013

Chem. Commun., 2013,49, 10160-10162

Permissions

Request permissions

Gated access to α-lithiated phenyltetrahydrofuran: functionalisation via direct lithiation of the parent oxygen heterocycle

R. Mansueto, V. Mallardo, F. M. Perna, A. Salomone and V. Capriati, Chem. Commun., 2013, 49, 10160 DOI: 10.1039/C3CC45499A

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