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

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.