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A Bioinspired Ugi/Michael/Aza-Michael Cascade Reaction in Aqueous Media: Natural-Product-like Molecular Diversity


  • S.S. and P.R.A. would like to thank Dr. Mary Jane Heeg (Wayne State University) for crystallographic data. P.R.A. acknowledges WSU for financial support and the NIH/NCI for an R03 CA153936-01 grant.


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Whole in one! A one-pot microwave-assisted reaction sequence that consists of an Ugi/Michael/aza-Michael transformation gives access to quaternary spirocenters leading to Amaryllidaceae and Erythrina alkaloid like compounds (see scheme). The process produces four stereogenic centers and six contiguous bonds, and provides products with good to excellent yields and appreciable diastereoselectivity.