Asymmetric synthesis of N-1-(heteroaryl)ethyl-N-hydroxyureas

Add time:08/14/2019    Source:sciencedirect.com

The asymmetric synthesis of two 5-lipoxygenase inhibitors (R)-N-1-(benzofuran-2-yl)ethyl-N-hydroxyurea, 99% ee, and (R)-N-1-(benzo[b]thiophen-2-yl)ethyl-N-hydroxyurea, 95% ee, is described. The enantioselective reduction of 1-(benzofuran-2-yl)ethanone oxime O-benzyl ether and 1-(benzo[b]thiophen-2-yl)ethanone oxime O-benzyl ether with borane oxazaborolidine, generated from (1R,2S,3R,4S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, was used for the formation of the stereogenic centres.

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