Unusual Magnesium Chloride Catalyzed Non‐Evans anti‐Aldol Reactions of an Enolizable L‐Threose Derivative

Abstract The magnesium chloride catalyzed anti ‐aldol reaction of phenyl acetate derived oxazolidinones proceeds readily with enolizable L ‐threose derivative 8 to provide anti ‐aldol adducts in high yields and with very high diastereoselectivities. The reaction is also efficient with aromatic aldehydes and provides slightly lower diastereoselectivities. This extension allows access to stereochemically defined fragments applicable to the synthesis of alkaloid and phenylpropanoid derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)