Synthesis of dihydronaphthalenes via aryne Diels-Alder reactions: scope and diastereoselectivity.
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.
Dockendorff
Chris
C
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
Sahli
Stefan
S
Olsen
Madeline
M
Milhau
Ludovic
L
Lautens
Mark
M