Asymmetric Cyclopropanation and Aziridination Reactions of Olefins Catalyzed by Cu(I)-Binaphthyldiimine Complexes

Autor: Suga, Hiroyuki, Kakehi, Akikazu, Ito, Suketaka, Ibata, Toshikazu, Fudo, Tomomi, Watanabe, Yuzuru, Kinoshita, Yoshinori
Zdroj: Bulletin of the Chemical Society of Japan; January 2003, Vol. 76 Issue: 1 p189-199, 11p
Abstrakt: The chiral Cu(I)-N,N′-bis(2,6-dichlorobenzylidene)-1,1′-binaphthyl-2,2′-diamine complex was found to be an efficient catalyst for asymmetric cyclopropanation and aziridination reactions of olefins with l-menthyl diazoacetate and [N-(p-tolylsulfonyl)imino]phenyliodinane, respectively. Among mono- and disubstituted olefins, 1,1-diarylethylenes showed extremely high enantioselectivities (up to 98% ee) in the cyclopropanation reactions in the presence of a chiral Cu(I)-catalyst (2 mol%). In the case of aziridination reactions catalyzed by the same Cu(I)-catalyst (10 mol%), the reaction of trans-substituted 3-aryl-2-propenoates and 1-substituted trans-3-aryl-2-propen-1-ones showed satisfactory results in term of the enantioselectivities (up to 98% ee).
Databáze: Supplemental Index