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Synlett 2001; 2001(1): 0013-0021
DOI: 10.1055/s-2001-9690
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The Double Annulation of Tethered Diacids and Alkynones: History and Scope

Robert B. Grossman*
  • *Department of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USA; Fax (859)323-1069; E-mail: rbgros1@pop.uky.edu
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Publication History

Publication Date:
31 December 2001 (online)

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The double Michael reaction of a tethered carbon diacid (a 1,n-dinucleophile) with an alkynone (a 1,1-dielectrophile) provides highly substituted and functionalized monocyclic double Michael adducts in what is formally an [n + 1] annulation. The pendant functionality in the double Michael adduct can be used to effect a second annulation. A history and overview of the "double annulation" route to bicyclic compounds is presented. The scope and selectivity of the route is also discussed.

bicyclic compounds - Michael additions - annulations - aminations - acylations