@article{1f34e49e344c4292ba6ed16c9957069d,
title = "Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[33.1]nonan-3-one Oximes",
abstract = "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.",
keywords = "1-(alkoxyamino)-adamantanes, 1-aminoadamantanes, amantadine, aza-Prins reaction, oxime",
author = "Tetsuya Kuga and Yusuke Sasano and Masaki Tomizawa and Masatoshi Shibuya and Yoshiharu Iwabuchi",
note = "Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Advanced Molecular Transformations by Organocatalysis{\textquoteright} (No. 23105011) from MEXT, {\textquoteleft}Precisely Designed Catalysts with Customized Scaffolding{\textquoteright} (No. JP16H00998) from JSPS, and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from the Japan Agency for Medical Research and Development (AMED), Japan.Mnisrtyi of Educoaitn, Cuutler, Sporst, Secince and Technoolgy 2(3105011aJ)pan Soeciy ofr hte Pormooitn of Secince PJ(16H00998) Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",
year = "2018",
month = may,
day = "2",
doi = "10.1055/s-0036-1591920",
language = "English",
volume = "50",
pages = "1820--1826",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "9",
}