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Author Notes:
Correspondence: Albert Padwa, Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322; Tel: +1 404 7270283; Fax: +1 404 7276629; Email: chemap@emory.edu or Scott K. Bur, Department of Chemistry, Gustavus Adolphus College, 800 West College Avenue, Saint Peter, MN 56082; Tel.: +1 507 9337038; Fax: +1 507 9337320;Email: sbur@gustavus.edu
Subject:
Research Funding:
AP wishes to acknowledge the research support of our cascade program in heterocyclic chemistry by the National Institutes of Health (GM 0539384) and the National Science Foundation (CHE-0450779).
Keywords:
- Cascade
- domino
- cycloaddition
- rearrangement
- electrocyclization
- sigmatropic
- metathesis
The Domino Way to Heterocycles
Abstract:
Sequential transformations enable the facile synthesis of complex target molecules from simple building blocks in a single preparative step. Their value is amplified if they also create multiple stereogenic centers. In the ongoing search for new domino processes, emphasis is usually placed on sequential reactions which occur cleanly and without forming by-products. As a prerequisite for an ideally proceeding one-pot sequential transformation, the reactivity pattern of all participating components has to be such that each building block gets involved in a reaction only when it is supposed to do so. The development of sequences that combine transformations of fundamentally different mechanisms broadens the scope of such procedures in synthetic chemistry. This mini review contains a representative sampling from the last 15 years on the kinds of reactions that have been sequenced into cascades to produce heterocyclic molecules.
Copyright information:
© 2007 Elsevier Ltd. All rights reserved.
This is an Open Access work distributed under the terms of the Creative Commons Attribution-NonCommerical-NoDerivs 3.0 Unported License (http://creativecommons.org/licenses/by-nc-nd/3.0/).
