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

Ying Wang; Wei Yuan; Hu-Fei Zheng; De-Qing Shi

doi:10.1055/s-0032-1317956

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(3): 382-388
DOI: 10.1055/s-0032-1317956

paper

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

Ying Wang

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Fax: 0086(27)67862041 eMail: chshidq@mail.ccnu.edu.cn

,

Wei Yuan

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Fax: 0086(27)67862041 eMail: chshidq@mail.ccnu.edu.cn

,

Hu-Fei Zheng

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Fax: 0086(27)67862041 eMail: chshidq@mail.ccnu.edu.cn

,

De-Qing Shi*

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Fax: 0086(27)67862041 eMail: chshidq@mail.ccnu.edu.cn

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Abstract

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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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Referenzen

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