4b-Aryltetrahydroindeno[1,2-a]indenes by Acid-Catalyzed Trans­annular Cyclization of Benzannulated Cyclooctene Alcohols

Dedicated to the late Professor Robert H. Grubbs

Abstract

By starting from two simple building blocks, benzannulated cyclooctenones were obtained in three steps. Subsequent Grignard/aryl lithium addition to the ketone yielded the corresponding tertiary alcohols that underwent stereoselective acid-catalyzed transannular cyclization to provide a cis-fused 5/5 bicyclic indanylindane framework exclusively. Subsequent stereoselective nucleophilic addition to the indanyl cation by hydride, water, or electron-rich aromatics furnished the 4b-aryltetrahydroindano[1,2-a]indenes in good to excellent yields (up to 92%) in the trans-C9–C9a form in up to a >99:1 diastereomeric ratio.

Key words

carbocations - cyclization - diastereoselectivity - metathesis - acid catalysis - indenoindenes

• References and Notes

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