Anion Relay Chemistry:  An Effective Tactic for Diversity Oriented Synthesis

Amos B. Smith, III* and Ming Xian
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104
J. Am. Chem. Soc., 2006, 128 (1), pp 66–67
DOI: 10.1021/ja057059w
Publication Date (Web): December 13, 2005
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, smithab@sas.upenn.edu

Abstract

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An effective one-flask multicomponent linchpin coupling protocol employing the concept of anion relay chemistry (ARC) was developed. This concept calls for addition of an anion (5) to an epoxide (6), bearing on a distal carbon a trialkyl silyl group and an anion stabilizing group (ASG), to furnish upon epoxide ring opening oxyanion 7. Addition of HMPA or other polar solvents to trigger a solvent controlled 1,4-Brook rearrangement then leads to a new distal anion (8), which in turn is available to react with a variety of second electrophiles.

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History

  • Published In Issue January 11, 2006
  • Received October 17, 2005

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