Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2009

Journal or Book Title

Organic Letters

Volume

11

Issue

1

First Page

69

Last Page

72

DOI

10.1021/ol802364c

Abstract

The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives, whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tail arrangement of the repeat units, the newly synthesized “clicked” oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.

Comments

Reprinted (adapted) with permission from Organic Letters 11 (2009): 69, doi:10.1021/ol802364c. Copyright 2009 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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