Y. Matsumura et al., New enantiomerically pure 1,2-dihydropyridine and its use for constructionof optically active 2-azabicycio[2.2.2] octane, TETRAHEDR L, 41(40), 2000, pp. 7685-7689
An enantiomerically pure 1,2-dihydropyridine 1 was prepared from L-lysine u
tilizing 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 exp
loited. That is, the presence of AlCl3 efficiently promoted the Diels-Alder
reaction to give a cycloadduct with high stereoselectivity, which was conv
erted to an optically active 2-azabicyclo[2.2.2]octane derivative 2 (96.8%
ee). (C) 2000 Elsevier Science Ltd. All rights reserved.