Journal of the Chemical Society. Perkin transactions II p. 1645 - 1648 (1983)
Update date:2022-09-26
Topics: Chiral Nucleophile Organometallic reagents Condensation Reactions Stereoselectivity
Alvarez-Ibarra, Carlos
Arjona, Odon
Perez-Ossorio, Rafael
Perez-Rubalcaba, Alfredo
Quiroga, Maria L.
Santesmases, Maria J.
Stereochemical results of the condensation reactions of a series of ketones, PhCHMeCOR (R= Me, Et, Pri, But, Ph), with various organomagnesium and organolithium derivatives in ethers as solvents are reported.Results are accounted for on the basis of competition between two transition states which may adopt either Karabatsos- or Felkin-type conformations according to the nature of R, the reagent nucleophilicity, and the polarity of solvent.Polar and steric analysis of this reaction allows highly stereoselective syntheses of diastereoisomeric α-phenylalkanols to be devised.
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