Oxa-Diels–Alder Reaction of Isatins and Acyclic α,β-Unsaturated Methyl Ketones through Cooperative Dienamine and Metal Lewis Acid Catalysis

Lu Liu; Philias Daka; Ryan Sarkisian; Yongming Deng; Kraig Wheeler; Hong Wang

doi:10.1055/s-0033-1338613

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(10): 1339-1347
DOI: 10.1055/s-0033-1338613

special topic

Oxa-Diels–Alder Reaction of Isatins and Acyclic α,β-Unsaturated Methyl Ketones through Cooperative Dienamine and Metal Lewis Acid Catalysis

Lu Liu

^aDepartment of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA eMail: wangh3@miamioh.edu

^bDepartment of Chemistry, East China Normal University, Shanghai 200062, P. R. of China

,

Philias Daka

^aDepartment of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA eMail: wangh3@miamioh.edu

,

Ryan Sarkisian

^aDepartment of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA eMail: wangh3@miamioh.edu

,

Yongming Deng

^aDepartment of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA eMail: wangh3@miamioh.edu

,

Kraig Wheeler

^cDepartment of Chemistry, Eastern Illinois University, 600 Lincoln Ave., Charleston, IL 61920, USA

,

Hong Wang*

^aDepartment of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA eMail: wangh3@miamioh.edu

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Abstract

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Abstract

Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels–Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58–86%), moderate stereoselectivities (1.3:1–5.9:1 dr, 50–81% ee), and excellent chemoselectivity.

Key words

bifunctional catalysis - tandem reactions - Yb(OTf)₃ - oxa-Diels–Alder reaction - spirooxindoles - tetrahydropyranones

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Referenzen

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7 CCDC 980769 contains crystallographic data of 3g. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif or by writing to the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk.

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