Asymmetric Methallylation of Ketones Catalyzed by a Highly Active Organocatalyst 3,3′‑F2‑BINOL

Zhang, Yongda; Li, Ning; Qu, Bo; Ma, Shengli; Lee, Heewon; Gonnella, Nina C.; Gao, Joe; Li, Wenjie; Tan, Zhulin; Reeves, Jonathan T.; Wang, Jun; Lorenz, Jon C.; Li, Guisheng; Reeves, Diana C.; Premasiri, Ajith; Grinberg, Nelu; Haddad, Nizar; Lu, Bruce Z.; Song, Jinhua J.; Senanayake, Chris H.

doi:10.1021/ol400498a.s001

ol400498a_si_001.pdf (5.88 MB)

Asymmetric Methallylation of Ketones Catalyzed by a Highly Active Organocatalyst 3,3′‑F₂‑BINOL

journal contribution

posted on 2013-04-05, 00:00 authored by Yongda Zhang, Ning Li, Bo Qu, Shengli Ma, Heewon Lee, Nina C. Gonnella, Joe Gao, Wenjie Li, Zhulin Tan, Jonathan T. Reeves, Jun Wang, Jon C. Lorenz, Guisheng Li, Diana C. Reeves, Ajith Premasiri, Nelu Grinberg, Nizar Haddad, Bruce Z. Lu, Jinhua J. Song, Chris H. Senanayake

(S)-3,3′-F₂-BINOL has been synthesized for the first time and demonstrated as a highly active organocatalyst for asymmetric methallylation of ketones. Up to 98:2 enantioselectivity and 99% yield were obtained with 5 mol % catalyst loading. The catalyst (S)-3,3′-F₂-BINOL could be easily recovered and reused.