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

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

• References


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