Synlett 2019; 30(20): 2209-2215
DOI: 10.1055/s-0037-1611921
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© Georg Thieme Verlag Stuttgart · New York

The Trouble with Five: New Synthetic Strategies toward C5 -Symmetric Pillar[5]arenes and Beyond

Ke Du
,
Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Rd., Nankai Dist., Tianjin 300072, P. R. of China   Email: andrew.sue@tju.edu.cn
› Author Affiliations
This work was supported by the 973 National Basic Research Program of China (2015CB856500) and the National Thousand Young Talents Program of China.
Further Information

Publication History

Received: 28 June 2019

Accepted after revision: 16 August 2019

Publication Date:
03 September 2019 (online)

Abstract

Rim-differentiated pillar[5]arenes (P[5]s) are intriguing macrocyclic molecular platforms with C 5-symmetry, but their conventional statistical syntheses suffer from low yields and laborious separation. Our group recently reported a ‘pre-oriented’ protocol that results in highly selective production of C 5-symmetric P[5]s among four constitutional isomers. Subsequently, we devised a more general divergent synthetic route starting with a common P[5] precursor with rim differentiation, followed by a series of high-yielding reactions that permit successive transformations of both rims freely. As a result, a variety of rim-differentiated P[5]s can be made to order in gram-scale quantities. This total solution not only populates the list of C 5-symmetric P[5]s, but also enables further design and synthesis of assorted five-fold organic building blocks towards complex supramolecular architectures.

 
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