Showing papers by "Matthias Breuning published in 2008"
TL;DR: The enantiomerically pure tricyclic 9-oxabispidine (1 R,2 S,9 S )-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0 2,7 ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S )-epichlorohydrin this article.
Abstract: The enantiomerically pure tricyclic 9-oxabispidine (1 R ,2 S ,9 S )-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0 2,7 ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and ( S )-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo -oriented side chain.
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