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Communication

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

Supporting Info

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

Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6

J. Am. Chem. Soc., 2005, 127 (43), pp 15028–15029

DOI: 10.1021/ja055498p

Publication Date (Web): October 5, 2005

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

, mlautens@chem.utoronto.ca

Abstract

Novel aryne Diels−Alder reactions with functionalized acyclic dienes are reported. These give useful cis-substituted dihydronaphthalene building blocks in good yield which are not easily accessible via other means, as demonstrated in the synthesis of sertraline. The first asymmetric aryne cycloaddition with an acyclic diene is also reported, giving excellent diastereoselectivities with Oppolzer's sultam as a chiral auxiliary.

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Published In Issue November 02, 2005
Received August 11, 2005

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Rational Design of Organocatalyst: Highly Stereoselective Michael Addition of Cyclic Ketones to Nitroolefins

Organocatalytic Enantioselective Friedel−Crafts Alkylation of 4,7-Dihydroindoles with α,β-Unsaturated Aldehydes: An Easy Access to 2-Substituted Indoles

Mitsunobu and Related Reactions: Advances and Applications

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