Asymmetric Domino Double Michael Addition of Nitroolefins and Aldehyde Esters with trans-Perhydroindolic Acid as an Organocatalyst

Abstract

An asymmetric domino double Michael addition reaction was developed using accessible substrates to construct biologically important and synthetically challenging cyclopentanes with four contiguous stereocenters. The proline-like molecules, trans-perhydroindolic acids, proved to be efficient organocatalysts in this reaction. Under the optimal reaction conditions, the asymmetric domino double Michael addition provided good yields (up to 98%), and excellent diastereoselectivities (up to 100% dr) and enantioselectivities (up to 99% ee). The obtained polysubstituted aliphatic cyclopentanes not only exist in biologically active natural products and medicines, but can also be converted into many other useful scaffolds via a simple transformation, such as cis-fused bicyclic lactams. Our current methodology is suitable for the synthesis of polysubstituted aliphatic cyclopentanes with contiguous multiple stereocenters.

Key words

polysubstituted aliphatic cycloalkanes - trans-perhydroindolic acids - organocatalyst - domino double Michael addition - bicyclic lactam

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