Organic & Biomolecular Chemistry 2011-10-07

Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: steering the C/O-chemoselectivity to reach tetrahydrobenzofuranones.

Rema B Devi, Matthias Henrot, Michaël De Paolis, Jacques Maddaluno

Index: Org. Biomol. Chem. 9(19) , 6509-12, (2011)

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Abstract

An unprecedented domino synthesis of tetrahydrobenzofuran-4-ones is described implicating chemoselective alkylation of various 1,3-cyclohexanediones with bromocrotonate or crotonitrile followed by oxa-Michael cyclization. Further transformations of this core to reach molecular diversity are also presented.