Use of Cleavable Coordinating Rings as Protective Groups in the Synthesis of a Rotaxane with an Axis that Incorporates More Chelating Groups Than Threaded Macrocycles

作者：Joosten Antoine; Trolez Yann; Heitz Valerie^*; Sauvage Jean Pierre

来源：Chemistry - A European Journal, 2013, 19(38): 12815-12823.

DOI：10.1002/chem.201301717

• click chemistry
• copper
• molecular machine
• protecting groups
• rotaxanes

A new methodology allowing preparation of a linear unsaturated [3]rotaxane consisting of an axis incorporating more coordination sites than threaded rings was developed. It was based on the preliminary synthesis of a saturated [5]rotaxane consisting of a four-chelating site axis threaded through four macrocyclic components, two of them being cleavable rings incorporating a lactone function and the two others being secure non-cleavable rings. The stoppering reaction was based on click chemistry. Subsequently, cleavage and removal of the two lactone-containing macrocycles from the [5]rotaxane in basic medium afforded the desired unsaturated [3]rotaxane in quantitative yield.

• 出版日期2013-9-16