Asymmetric Synthesis of 2,2-Disubstituted Benzofuranones through an Organocatalytic Alkylation with Nitroallylic Acetates

Abstract

The asymmetric allylic alkylation of benzofuran-3(2H)-ones with nitroallylic acetates has been achieved employing a bifunctional thiourea organocatalyst via S_N2′ substitution. A series of 2,2-disubstituted benzofuranones bearing adjacent tetrasubstituted and tertiary stereocenters have been synthesized with moderate to good yields and very good stereoselectivities.

Key words

allylic alkylation - benzofuranones - nitroallylic acetates - organocatalysis­ - asymmetric synthesis

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