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

作者：An, Qianjin; Shen, Jiefeng; Butt, Nicholas; Liu, Delong^*; Liu, Yangang; Zhang, Wanbin

来源：Synthesis (Germany), 2013, 45(12): 1612-1623.

DOI：10.1055/s-0033-1338839

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

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.

• 出版日期2013-6
• 单位上海交通大学