Multicomponent Cycloadditions:  The Four-Component [5+1+2+1] Cycloaddition of Vinylcyclopropanes, Alkynes, and CO

Paul A. Wender,* Gabriel G. Gamber, Robert D. Hubbard, Son M. Pham, and Lei Zhang
Stanford University, Department of Chemistry, Stanford, California 94305-5080
J. Am. Chem. Soc., 2005, 127 (9), pp 2836–2837
DOI: 10.1021/ja042728b
Publication Date (Web): February 11, 2005
Copyright © 2005 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.

, wenderp@stanford.edu

Abstract

Abstract Image

Prompted by the view that intermediates of transition metal-catalyzed reactions could be intercepted by one or more additional components, studies in our laboratory have led to the design and development of new three-component [5+2+1], [4+2+1], and [2+2+1] cycloadditions. These continuing studies have now led to the identification of a fundamentally new four-component [5+1+2+1] cycloaddition reaction of vinylcyclopropanes, alkynes and CO, yielding hydroxyindanone products in generally good yields. Terminal alkynes bearing aryl or alkyl groups are tolerated well. Substitution at any position of the VCP leads predictably to substituted hydroxyindanone products. Using a bis-alkynyl substrate, the reaction can be carried out bi-directionally, forming 10 C−C bonds and four new rings from seven components in a single, operationally simple process.

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History

  • Published In Issue March 09, 2005
  • Received December 2, 2004

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