Enantioselective synthesis of functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones via Michael–hemiaminalization/oxidation reaction†
Abstract
A novel method is developed for the enantioselective synthesis of highly functionalized 3,4-disubstituted dihydro-2(1H)-quinolinones bearing two trans contiguous stereogenic centers with excellent diastereoselectivities (up to >99 : 1 dr) and high to excellent enantioselectivities (up to >99% ee). The process combines an enantioselective organocatalytic Michael–hemiaminalization reaction and a highly efficient oxidation reaction sequence with good yields and stereoselectivity.