Kinetic Resolution of Constitutional Isomers Controlled by Selective Protection Inside a Supramolecular Nanocapsule

Overview

Journal Nat Chem

Specialty Chemistry

Date 2010 Sep 24

PMID 20861900

Citations 21

Authors

Simin Liu

Haiying Gan

Andrew T Hermann

Steven W Rick

Bruce C Gibb

Affiliations

Soon will be listed here.

Abstract

The concept of self-assembling container molecules as yocto-litre reaction flasks is gaining prominence. However, the idea of using such containers as a means of protection is not well developed. Here, we illustrate this idea in the context of kinetic resolutions. Specifically, we report on the use of a water-soluble, deep-cavity cavitand to bring about kinetic resolutions within pairs of esters that otherwise cannot be resolved because they react at very similar rates. Resolution occurs because the presence of the cavitand leads to a competitive binding equilibrium in which the stronger binder primarily resides inside the host and the weaker binding ester primarily resides in the bulk hydrolytic medium. For the two families of ester examined, the observed kinetic resolutions were highest within the optimally fitting smaller esters.

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