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

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 AlCl3 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). (C) 2000 Elsevier Science Ltd. All rights reserved.