Download PDF
Synfacts 2007(11): 1205-1205  
DOI: 10.1055/s-2007-991245
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Enantioselective Protonation of Silyl Enolates

Contributor(s): Benjamin List, Daniela Kampen
T. Poisson, V. Dalla, F. Marsais, G. Dupas, S. Oudeyer, V. Levacher*
INSA-Université de Rouen and Université du Havre, France
Further Information

Publication History

Publication Date:
23 October 2007 (online)

    Permissions and Reprints

Significance

An enantioselective protonation of silyl enolates using an organocatalyst and a latent source of HF has been developed. Cinchona alkaloid 1 (10 mol%) mediates the reaction of silyl enol ethers 2 with HF, generated in situ from PhCOF and EtOH, to the corresponding ketones 3 in good yields and enantioselectivities. The underlying catalytic cycle presumably involves the HF salt of tertiary amine 1 and is based on the high affinity of silicon for fluorine.