Synthesis 2014; 46(10): 1339-1347
DOI: 10.1055/s-0033-1338613
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Lu Liu
a  Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA   Email: wangh3@miamioh.edu
b  Department of Chemistry, East China Normal University, Shanghai 200062, P. R. of China
,
Philias Daka
a  Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA   Email: wangh3@miamioh.edu
,
Ryan Sarkisian
a  Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA   Email: wangh3@miamioh.edu
,
Yongming Deng
a  Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA   Email: wangh3@miamioh.edu
,
Kraig Wheeler
c  Department of Chemistry, Eastern Illinois University, 600 Lincoln Ave., Charleston, IL 61920, USA
,
Hong Wang*
a  Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA   Email: wangh3@miamioh.edu
› Author Affiliations
Further Information

Publication History

Received: 14 January 2014

Accepted after revision: 25 February 2014

Publication Date:
26 March 2014 (eFirst)

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.

Supporting Information

 
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