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Solid-phase rhodium carbenoid reactions: An N-H insertion route to a diverse series of oxazoles

Academic Article
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Overview

authors

  • Clapham, B.
  • Spanka, C.
  • Janda, Kim

publication date

  • July 2001

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] The solid-phase synthesis of a series of oxazoles is described. The key step in the construction of these molecules involves the rhodium-catalyzed decomposition of polymer-bound alpha-diazo-beta-ketoesters. These reactions are performed in the presence of primary amides and yield the corresponding N-H insertion products. Subsequent cyclodehydration of these alpha-(acylamino)-beta-ketoesters provides the corresponding resin-bound 2,5-disubstituted oxazoles, which are further elaborated during cleavage from the resin.

subject areas

  • Amines
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Cyclization
  • Models, Chemical
  • Molecular Structure
  • Oxazoles
  • Rhodium
  • Stereoisomerism
  • Structure-Activity Relationship
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol010075n

PubMed ID

  • 11440572
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Additional Document Info

start page

  • 2173

end page

  • 2176

volume

  • 3

issue

  • 14

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