Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes
An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.
2003 ◽
Vol 134
(3)
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pp. 445-451
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2012 ◽
Vol 51
(22)
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pp. 5367-5370
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1991 ◽
Vol 21
(14)
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pp. 1489-1500
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2017 ◽
Vol 15
(48)
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pp. 10200-10211
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