Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols

Autor:	Naomichi Miyairi, Ken Ichi Ichikawa, Naoya Hosoda, Suguru Ito, Yukihiro Sasahara, Masatoshi Asami
Rok vydání:	2015
Předmět:	Benzaldehyde chemistry.chemical_compound chemistry 1-Phenylethylamine Organic Chemistry Drug Discovery Enantioselective synthesis Organic chemistry Cyclohexanone Diethylzinc Biochemistry Pyrrolidine Catalysis
Zdroj:	Tetrahedron. 71:6796-6802
ISSN:	0040-4020
DOI:	10.1016/j.tet.2015.07.031
Popis:	A series of o-xylylene-type 1,4-amino alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since the stereochemical outcome of the reaction was controlled by the chiral benzylic carbon bearing amino group. Highest catalytic activity was obtained by using (R)-1-{2-[1-(pyrrolidin-1-yl)ethyl]phenyl}cyclohexan-1-ol (1n) derived from (R)-1-(1-phenylethyl)pyrrolidine and cyclohexanone. Various chiral secondary alcohols were obtained by the reaction of diethylzinc and aldehydes in the presence of 1n within 2 h with good to high enantioselectivities.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6ab1638a01422f8fae400fbafb3baf8f https://doi.org/10.1016/j.tet.2015.07.031 Zobrazit plný text záznamu Full Text from ScienceDirect