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05 Jan 20:41

Zirconium-Catalyzed Desymmetrization of Aminodialkenes and Aminodialkynes through Enantioselective Hydroamination

by Kuntal Manna, Naresh Eedugurala and Aaron D. Sadow

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/ja511250m
31 May 19:59

A Bioinspired Catalytic Oxygenase Cascade to Generate Complex Oxindoles

by Yao Wang, Jonathan O. Bauer, Carsten Strohmann, Kamal Kumar

Abstract

Catalytic, selective, and controlled oxidative functionalization of C[BOND]H bonds using molecular oxygen as an oxidant remains highly desirable and equally challenging in the development of synthetic methodologies. Presented herein is a one-pot oxygenase cascade reaction wherein a copper(I)-catalyzed oxygenase reaction transforms the allylic methyl group in 3-methylidene oxindoles into an aldehyde, which then undergoes an aldol–oxa-Michael addition sequence with β-ketoesters to yield dihydrofuran-bearing oxindoles.

Thumbnail image of graphical abstract

O2 cascades: The first one-pot oxygenase cascade is presented, wherein a copper-catalyzed oxygenase reaction transforms the allylic CH3 of 3-methylidene oxindole into an aldehyde, which then undergoes an aldol–oxa-Michael addition reaction with β-ketoesters to give dihydrofuran-bearing oxindoles.