Chiral environment specifically induced by metal ion: Asymmetric α-alkylation of α-amino esters using pyridoxal derivatives having a chiral ionophore function

Autor:	Chiaki Kurozumi, Hideto Miyabe, Kuninori Tai, Kazuyuki Miyashita, Hiroshi Iwaki, Takeshi Imanishi
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Aldimine Amino esters Stereochemistry Organic Chemistry Ionophore Alkylation Biochemistry Hydrolysis chemistry.chemical_compound chemistry Drug Discovery Side chain Stereoselectivity Pyridoxal
Zdroj:	Tetrahedron. 55:12109-12124
ISSN:	0040-4020
Popis:	Stereoselective alkylation of aldimines, prepared from α-amino esters and pyridoxal models having an ionophoric side-chain composed of a chiral glycerol structure, proceeded in the presence of Li+ or Na+ to afford α,α-dialkyl amino esters after acidic hydrolysis. Both the structure of the side chain and the metal ion were found to be in relation with the stereoselectivity, affording the highest stereoselectivity when the side-chain having a 2-naphthylmethoxy group and a methoxy group at the respective 3′- and 2′-positions was employed in the presence of Na+.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7babf22d73efba8c0a21d4040f72e13b https://doi.org/10.1016/s0040-4020(99)00708-5 Zobrazit plný text záznamu Full Text from ScienceDirect