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Synthesis of Dihydronaphthalenes via Aryne Diels-Alder Reactions: Scope and Diastereoselectivity

Chris Dockendorff, Stefan Sahli, Madeline Olsen, Ludovic Milhau and Mark Lautens*

*Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6, Email: mlautenschem.utoronto.ca

C. Dockendorff, S. Sahli, M. Olsen, L. Milhau, M. Lautens, J. Am. Chem. Soc., 2005, 127, 15028-15029.

DOI: 10.1021/ja055498p (free Supporting Information)


Abstract

Aryne Diels-Alder reactions with functionalized acyclic dienes give useful cis-substituted dihydronaphthalene building blocks in good yield. Asymmetric aryne cycloadditions with Oppolzer's sultam as a chiral auxiliary are also reported .


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Key Words

Diels-Alder Reaction, [4+2]-cycloadditions


ID: J48-Y2005-2710