Substituted 3(2H)‐Furanones by a Tandem Michael Addition/Palladium‐Catalyzed Ring‐Closing Protocol. Issue 5 (4th January 2013)

• Record Type: Journal Article
• Authors: John, Jubi; Hopf, Henning
• Is Part Of: European journal of organic chemistry. Issue 5(2013)
• Page Start: 841
• Page End: 845
• Publication Date: 2013-01-04
• Subjects: Homogeneous catalysis -- Palladium -- Domino reactions -- Michael addition -- Oxygen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201253
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel palladium‐catalyzed route for the synthesis of substituted 3(2 H )‐furanones from activated alkenes and 4‐chloroacetoacetate was developed. The first step of the tandem reaction is the Michael addition of an acetoacetate to the alkene followed by palladium‐catalyzed ring closure of the adduct to form the furanone. The reaction was extended to a number of substituted alkenes, and the corresponding substituted 3(2 H )‐furanones were obtained in good to excellent yields. Abstract : Substituted 3(2 H )‐furanones are synthesized in good to excellent yields by the palladium‐catalyzed reaction of 4‐chloroacetoactate with activated styrenes. The tandem reaction starts with Michael addition of an acetoacetate to the activated alkene followed by palladium‐catalyzed ring closing of the primary adduct to form the furanone.