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

✍ Scribed by Yoshihiro Matsumura; Yasuharu Nakamura; Toshihide Maki; Osamu Onomura

Book ID
104210893
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
116 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

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).

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ChemInform Abstract: New Enantiomericall
ChemInform Abstract: New Enantiomerically Pure 1,2-Dihydropyridine and Its Use for Construction of Optically Active 2-Azabicyclo[2.2.2]octane.
✍ Yoshihiro Matsumura; Yasuharu Nakamura; Toshihide Maki; Osamu Onomura πŸ“‚ Article πŸ“… 2000 πŸ› John Wiley and Sons βš– 30 KB πŸ‘ 1 views

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