Taco complex templated syntheses of a cryptand/paraquat [2]rotaxane and a [2]catenane by olefin metathesis

Org Lett. 2009 Aug 6;11(15):3350-3. doi: 10.1021/ol9012052.

Abstract

Taco complex templation based on the bis(m-phenylene)-32-crown-10/paraquat recognition motif is used to develop a general method for preparing mechanically interlocked molecules. A [2]rotaxane and a [2]catenane were synthesized in high yields by a ring-closing metathesis reaction, which was owed to the impactful template effect. Due to the high symmetry of (5,5')-difunctional bis(m-phenylene)-32-crown-10 derivatives, this taco complex templated synthesis has potential to be a tempting method to solve a symmetry-based problem in the fabrication of complicated mechanically interlocked structures.