Formation of Four- to Six-Membered Carbocycles by Tandem Brook Rearrangement-Intramolecular Michael Reaction

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Abstract
A tandem Brook rearrangement-intramolecular Michael reaction has been developed as a synthetic route to functionalized carbocycles. Acylsilanes, tethered by a two-, three-, or four-carbon chain to an acrylate Michael acceptor, have been prepared and used as the cyclization substrates. Treatment of these compounds with PhLi or LiP(O)(OMe)2 at temperatures below 0 °C results in the formation of four- to six-membered carbocycles in good yields.

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