Azetidine-derived bifunctional organocatalysts for Michael reactions

Add time:09/26/2019    Source:sciencedirect.com

2-Cyano azetidines, easily accessible from β-amino alcohols, are precursors of stereodefined homochiral azetidinic or pyrrolidinic 1,2-diamines. A small library of these original diamines was screened as precatalysts for the enantioselective addition of 1,3-dicarbonyl compounds onto β-nitro styrenes. An azetidinic diamine derived from (−)-ephedrine and derivatized as a thiourea was found to catalyze the conjugate addition of acetylacetone with good levels of enantioselectivities (up to 84% ee). Interestingly, the absolute configuration of the Michael adduct depends on the nature of the 1,3 dicarbonyl nucleophile (diethyl malonate or acetylacetone), which is indicative of a different mechanism involved in the reaction of these two nucleophiles.

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