Diastereo- and Enantioselective Synthesis of α,α′-Disubstituted,C 2-Symmetric Ketones Using the SAMP-/RAMP-Hydrazone Method
- 1 January 1991
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (12) , 1137-1141
- https://doi.org/10.1055/s-1991-28405
Abstract
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%).Keywords
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