Issue 14, 2014

Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent

Abstract

The regioselective lithiation–functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.

Graphical abstract: Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent

Supplementary files

Article information

Article type
Communication
Submitted
08 Nov 2013
Accepted
03 Dec 2013
First published
06 Dec 2013

Chem. Commun., 2014,50, 1698-1700

Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent

L. Degennaro, M. Zenzola, P. Trinchera, L. Carroccia, A. Giovine, G. Romanazzi, A. Falcicchio and R. Luisi, Chem. Commun., 2014, 50, 1698 DOI: 10.1039/C3CC48555B

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