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Synfacts 2008(6): 0617-0617  
DOI: 10.1055/s-2008-1078398
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral α-Substituted Ketones via Enantioselective Protonation

Contributor(s): Mark Lautens, Frédéric Ménard
S. C. Marinescu, T. Nishimata, J. T. Mohr, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

The above catalytic system improved the generality of a previous protocol reported by the same authors (J. Am. Chem. Soc. 2006, 128, 11348; Synfacts 2006, 1239). Whereas the original procedure using HCO2H as proton source needed tuning of the reaction conditions for many substrates, the protocol using Meldrum’s acid is now applicable to a range of β-keto esters. The mildness of the reaction conditions is noteworthy.