Synthesis 2017; 49(05): 1009-1023
DOI: 10.1055/s-0036-1588681
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© Georg Thieme Verlag Stuttgart · New York

One-Step Synthesis of a Unique Molecular Platform for the Selective Functionalization of Calix[6]arenes

Roy Lavendommea, b, Volodymyr Malytskyia, Jeremy Vandermeerscha, Michel Luhmerb, Ivan Jabin*a
  • aLaboratoire de Chimie Organique, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: ijabin@ulb.ac.be
  • bLaboratoire de Résonance Magnétique Nucléaire Haute Résolution, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/08, 1050 Brussels, Belgium
Further Information

Publication History

Received: 24 October 2016

Accepted after revision: 01 December 2016

Publication Date:
03 January 2017 (eFirst)

Abstract

High selectivity is crucial for the functionalization of macrocyclic platforms bearing multiple identical functions. In the case of calix[6]arenes, only a few examples of efficient homo-functionalization have been reported. Herein, we describe the one-step synthesis of a tri-differentiated calix[6]arene and its use as a key intermediate to selectively access various homo- and hetero-functionalization patterns. In combination with the ‘all-but-one’ carbamatation methodology, this unique building block gives access to sophisticated calix[6]arenes that, until now, were inaccessible.

Supporting Information