Asymmetric Robinson-type annulation reaction between β-ketoamides and α,β-unsaturated ketones.

J Org Chem

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

Published: April 2015

Enantioselective Robinson-type annulation reaction between β-ketoamide and α,β-unsaturated ketone was developed by utilizing the amino acid derived primary-secondary diamine catalysts. The less reactive acyclic β-ketoamides employed as both electrophile and nucleophile are reported in this asymmetric tandem reaction. A number of chiral cyclohexenone derivatives containing an amide group were obtained in high yields and good selectivities.

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http://dx.doi.org/10.1021/jo502904nDOI Listing

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