Issue 11, 2009
From the journal:

Chemical Society Reviews

The development of endo-selective epoxide-opening cascades in water†

Christopher J. Morten,a   Jeffery A. Byers,a   Aaron R. Van Dyke,a   Ivan Vilotijevica  and  Timothy F. Jamison*a  

* Corresponding authors

a Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, USA
E-mail: tfj@mit.edu

Abstract

This tutorial review traces the development of endo-regioselective epoxide-opening reactions in water. Templated, water-promoted epoxide-opening cyclization reactions can offer rapid access to subunits of the ladder polyethers, a fascinating and complex family of natural products. This review may be of interest to those curious about the ladder polyethers and their hypothesized biogenesis, about organic reactions in water, and about the development and application of cascade reactions in organic synthesis.

Graphical abstract: The development of endo-selective epoxide-opening cascades in water

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Article information

DOI
https://doi.org/10.1039/B816697H
Article type
Tutorial Review
Submitted
03 Jun 2009
First published
16 Sep 2009

Chem. Soc. Rev., 2009,38, 3175-3192

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The development of endo-selective epoxide-opening cascades in water

C. J. Morten, J. A. Byers, A. R. Van Dyke, I. Vilotijevic and T. F. Jamison, Chem. Soc. Rev., 2009, 38, 3175 DOI: 10.1039/B816697H

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