Synthesis, Resolution and Absolute Configuration of 2,3-Dihydro-2-<i>Tert</i>-Butyl-3-<i>N</i>-Benzylquinazolin-4-One: A Possible Chiral Auxiliary for Synthesis of <i>β</i>-Amino Cyclohexancarboxylic Acid

Abstract

3-Benzyl-2-(tert-butyl)-2,3-dihydroquinazolin-4(1H)-one rac-11 was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a substrate chiral in asymmetric induction due to the steric effects of its tert-butyl group.