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2-Ethylquinazolin-4-one derivatives bearing various orthosubstituted phenyl groups were revealed to possess a stable C-N axially chiral structure at ambient temperature. The reactions of alkyl halides with the anionic species prepared from these quinazolinones were systematically explored. The a-alkylation reactions proceeded with diastereoselectivities ranging from 1:1 to >50:1, depending upon the steric bulk of the ortho-substituent, to afford products having the elements of axial and central chirality in high yields (85-98%). [ABSTRACT FROM AUTHOR]