Bifunctional Tertiary Phosphine-Catalyzed Cascade Michael–Henry Reaction of a β-Nitroolefin and a 2-(1-Substituted 3-oxo-3-phenylpropyl)malononitrile

Abstract

The bifunctional phosphine catalyst 2′-(diphenylphosphino)biphenyl-2-ol was used in an effective synthesis of highly functionalized cyclohexanols through a cascade Michael–Henry reaction of a β-nitroolefin and a 2-(1-substituted 3-oxo-3-phenylpropyl)malononitrile. The method has the advantages of requiring mild conditions and providing a convenient workup, high diastereoselectivity, good atom economy, and a wide substrate scope, rendering it useful for the synthesis of highly functionalized cyclohexanols.

Key words

alcohols - carbocycles - catalysis - cascade reactions

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