Journal of Organic Chemistry p. 2709 - 2712 (1981)
Update date:2022-08-05
Topics:
Taylor, Stephen K.
Lilley, Gay L.
Lilley, Kevin J.
McCoy, Patricia A.
Under catalytic conditions, trans-5,6-epoxy-cis-cyclodecene (1) undergoes a Friedel-Crafts (FC) reaction with various aromatic molecules.Four chiral centers are formed via transannular ring closure in this remarkably stereoselective FC reaction (Scheme I).The side products are all consistent with the proposed reaction intermediate, for which oxygen bridging is proposed to account for experimental observations.Geraniolene monoepoxide (14) was also investigated for transannular FC reactions.In this case, FC alkylation was observed (in low yield) only when anisole was the aromatic solvent.
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