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Synthesis 1991; 1991(12): 1137-1141
DOI: 10.1055/s-1991-28405
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Diastereo- and Enantioselective Synthesis of α,α′-Disubstituted, C 2-Symmetric Ketones Using the SAMP-/RAMP-Hydrazone Method

Dieter Enders* , Winfried Gatzweiler, Udo Jegelka
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany
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Publication Date:
29 April 2002 (online)

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Starting from simple, symmetric ketones such as, 3-pentanone,1, 3-diphenyl-2-propanone and 2,2-dimethyl-1,3-dioxan-.5-one, α,α′-bisalkylation of the corresponding SAMP-hydrazones (S)-2 and (S)-8 [(S)-1-(alkylideneamino)-2-(methoxymethyl)pyrrolidines and (S)-1-(2,2-dimethyl-1,3-dioxan-5-ylideneamino)-2-(methoxymethyl)pyrrolidines, respectively], followed by oxidative cleavage with ozone affords chiral, C2-symmetric ketones 5 and (S,S)-11 of high diastereo- and enantiomeric purity (de, ee > 98%).