New enantiomerically pure 1,2-dihydropyridine and its use for construction of optically active 2-azabicyclo[2.2.2]octane

Abstract

An enantiomerically pure 1,2-dihydropyridine 1 was prepared from l-lysine utilizing anodic oxidation as a key step, and was utilized as a chiral diene synthon of the Diels–Alder reaction. Furthermore, a suitable condition for the Diels–Alder reaction between 1 and N-acryloyloxazolidinone ( 8) was exploited. That is, the presence of AlCl 3 efficiently promoted the Diels–Alder reaction to give a cycloadduct with high stereoselectivity, which was converted to an optically active 2-azabicyclo[2.2.2]octane derivative 2 (96.8% ee).