Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro­furanyl Spirooxindoles

Dedicated to Professor Victor Snieckus on the occasion of his 80^th birthday

Abstract

An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

Key words

organocatalysis - domino reaction - enantioselectivity - heterocycles - Michael addition

• References

• 1 Present address: Department of Pathology, Michigan Medicine, University of Michigan, 1150 W. Medical Center Drive, Ann Arbor, Michigan 48109-5605, USA.

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