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Catalytic Enantioselective Tautomerization of Isolated Enols
Firmenich SA, Geneva, Switzerland
22 November 2007 (online)
This paper describes a nice unique method involving enantioselective tautomerization and protonation of isolated enols. Using catalytic lithiated chiral amino alcohol (1), slow addition of the isolated enol followed by warming from -78 °C to -40 °C and subsequent quenching with 5% aqueous HCl afforded the desired ketone with good ee. A nonlinear effect was observed pointing to higher order mixed aggregates being responsible for the asymmetric induction.