Abstract
2-Ethylquinazolin-4-one derivatives bearing various ortho -substituted 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 α-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%).
Original language | English |
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Journal | Synlett |
DOIs | |
Publication status | Accepted/In press - 2018 May 29 |
Keywords
- alkylation
- axial chirality
- diastereoselectivity
- quinazolinones
ASJC Scopus subject areas
- Organic Chemistry