New C2-symmetric 2,4-bis(1-hydroxycyclopentyl)azetidines derived from (S)-1-phenylethylamine and their application in the enantioselective catalysis

Add time:08/31/2019    Source:sciencedirect.com

The synthesis of new tridental 2,4-bis(1-hydroxycyclopentyl)azetidines using (S)-1-phenylethylamine as starting material is described. These new structures have been successfully applied in the enantiocontrolled catalytic addition of diethylzinc to aromatic aldehydes reaching enantiomeric excesses of up to 85% for the resulting 1-arylpropan-1-ols. Attempts in the field of the enantioselective oxazaborolidine-catalyzed reduction of ketones employing azetidine alcohols as precatalysts are also included.

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