Convenient asymmetric synthesis of both enantiomers of 3,4-disubstituted 3,4-dihydro-1,4-benzoxazin-2-ones

ABSTRACT

Both enantiomers of N-substituted 3-arylated 3,4-dihydro-1,4-benzoxazin-2-ones were conveniently synthesized up to 93:7 er based on the dynamic kinetic resolution of either (R)-pantolactone- or l-mandelate-derived α-bromo arylacetates in nucleophilic substitution with N-alkylated 2-aminophenols.

GRAPHICAL ABSTRACT

KEYWORDS:

• Asymmetric synthesis
• chiral auxiliary
• dihydrobenzoxazinone
• dynamic kinetic resolution
• nucleophilic substitution

Additional information

Funding

This paper was written as part of Konkuk University’s research support program for its faculty on sabbatical leave in 2015. This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1D1A1B03035502).