A general overview of the organocatalytic intramolecular aza-Michael reaction

作者:Sanchez Rosello Maria*; Acena Jose Luis; Simon Fuentes Antonio; del Pozo Carlos
来源:Chemical Society Reviews, 2014, 43(21): 7430-7453.
DOI:10.1039/c4cs00156g

摘要

The organocatalytic intramolecular aza-Michael reaction gives access to enantiomerically enriched nitrogen-containing heterocycles in a very simple manner. Enals, enones, conjugated esters and nitro olefins have been employed as Michael acceptors, while moderate nitrogen nucleophiles such as sulphonamides, carbamates and amides have been shown to be appropriate Michael donors in this type of reaction. Additionally, the process has been performed under both covalent and non-covalent catalysis, with diaryl prolinols, imidazolidinones, thioureas and chiral binol phosphoric acids being the most frequently used catalysts. The level of efficiency reached with this protocol is demonstrated by the implementation of numerous tandem processes, as well as the total synthesis of several natural products.

  • 出版日期2014