1449477-57-9Relevant academic research and scientific papers
Asymmetric domino double michael addition of nitroolefins and aldehyde esters with trans-perhydroindolic acid as an organocatalyst
An, Qianjin,Shen, Jiefeng,Butt, Nicholas,Liu, Delong,Liu, Yangang,Zhang, Wanbin
, p. 1612 - 1622 (2013/07/27)
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. Georg Thieme Verlag Stuttgart. New York.
