Asymmetric induction during organometallic conjugate addition to enantiomerically pure 2-(arylsulfinyl)-2-cyclopentenones

GH Posner, JP Mallamo, M Hulce…

Index: Posner, Gary H.; Mallamo, John P.; Hulce, Martin; Frye, Leah L. Journal of the American Chemical Society, 1982 , vol. 104, # 15 p. 4180 - 4185

Full Text: HTML

Citation Number: 71

Abstract

Abstract: Virtually complete asymmetric induction is achieved during methyl-, vinyl-, and naphthylmetallic conjugate addition to enantiomerically pure (S)-(+)-2-(p-tolylsulfinyl)-2- cyclopentenone ((S)-(+)-1).(R)-3-Methylcyclopentanone is obtained when the enone sulfoxide (S)-(+)-1 is first complexed with divalent zinc and then methylmagnesium iodide is added, whereas (S)-3-methylcyclopentanone is obtained when methylmagnesium iodide ...