Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.
A quinidine-catalyzed diastereoselective addition of α-angelica lactone to β-halo-α-ketoesters is reported. The α-angelica lactone displays unusual regioselectivity in this reaction, acting as a nucleophile at the α-position to provide fully substituted glycolic esters with three contiguous stereocenters. Subsequent diastereoselective hydrogenation provides an additional stereocenter within the lactone.
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Jessica A
JA
Griswold
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Matthew A
MA
Horwitz
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Leslie V
LV
Leiva
Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
Jeffrey S
0000-0001-8882-9881
JS
Johnson
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D004952:Esters; D006846:Hydrocarbons, Halogenated; D007659:Ketones; C019257:angelica lactone; D015107:4-Butyrolactone