Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine–Transition Metal Complexes. I. Preparation of Chiral Ferrocenylphosphines

Autor:	Keiji Yamamoto, Masahiro Kagotani, Mitsuo Konishi, Sota Kawakami, Tamio Hayashi, Akira Matsumoto, Motoo Fukushima, Yuji Hamada, Takaya Mise, Nobuo Nagashima, Makoto Kumada
Rok vydání:	1980
Předmět:	chemistry.chemical_compound chemistry Ferrocene Stereochemistry Side chain Enantioselective synthesis Nucleophilic substitution General Chemistry Ethyl group Ethylamine Planar chirality Medicinal chemistry Phosphine
Zdroj:	Bulletin of the Chemical Society of Japan. 53:1138-1151
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.53.1138
Popis:	As chiral ligands for transition metal complex catalyzed asymmetric reactions, various kinds of chiral ferrocenylphosphines, which have planar chirality due to 1,2-unsymmetrically substituted ferrocene structure and also have a functional group on the side chain of the ferrocene nucleus, were prepared. (S)-N,N-dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine [(S)-(R)-PPFA], (S)-N,N-dimethyl-1-[(R)-1′,2-bis(diphenylphosphino)ferrocenyl]ethylamine [(S)-(R)-BPPFA], and their dimethylphosphino derivatives were prepared by way of lithiation of optically resolved N,N-dimethyl-1-ferrocenylethylamine. The 1-(dimethylamino)ethyl group on the ferrocenylphosphines was converted stereospecifically by nucleophilic substitution reactions into 1-methoxy-, 1-hydroxy-, 1-diphenylphosphino-, and several 1-(dialkylamino)ethyl groups. 1-Diphenylphosphino-2-(dimethylaminomethyl)ferrocene (FcPN) was optically resolved via its phosphine sulfide dibenzoyltartaric acid salt. The relationship between CD spectra of the ch...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::df7dcd3e0b7d565f980790f3cfa284e5 https://doi.org/10.1246/bcsj.53.1138 Zobrazit plný text záznamu