Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts

Autor:	Masatoshi Asami, Miki Takano, Yoshitaka Takebe, Yoshitaka Yamaguchi, Naoya Hosoda, Hideaki Kamito
Rok vydání:	2013
Předmět:	Organic Chemistry Enantioselective synthesis Borane Biochemistry Pyrrolidine Catalysis Reduction (complexity) chemistry.chemical_compound chemistry Diamine Drug Discovery Organic chemistry Enantiomer Acetophenone
Zdroj:	Tetrahedron. 69:1739-1746
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.12.024
Popis:	Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl)pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c1179b2daf036775ff8e607628b5c034 https://doi.org/10.1016/j.tet.2012.12.024 Zobrazit plný text záznamu Full Text from ScienceDirect