Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

This paper is dedicated to Professor Dieter Enders on the occasion of his 70^th birthday. He has always been a source of inspiration to develop new cascade reactions.

Abstract

We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

Key words

synergistic catalysis - organocatalysis - cyclopentanes - asymmetric synthesis - cycloaddition

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