Asymmetric Methallylation of Ketones Catalyzed by a Highly Active Organocatalyst 3,3 '-F-2-BINOL

(S)-3,3'-F-2-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'-F-2-BINOL could be easily r...

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Published inOrganic letters Vol. 15; no. 7; pp. 1710 - 1713
Main Authors 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.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.04.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BINOL
CARBON CENTERS
LIGANDS
ALDOL REACTION
ALLYLBORATION
DIRECTED ORTHO-METALATION
CONSTRUCTION
VERSATILE CHIRAL REAGENT
ENANTIOSELECTIVE ALLYLATION
TRIMETHOXYSILYL ENOL ETHERS
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Summary:(S)-3,3'-F-2-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'-F-2-BINOL could be easily recovered and reused.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400498a