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Synthesis 1989; 1989(7): 493-496
DOI: 10.1055/s-1989-27298
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Enantioselective Alkylation of 2,2-Dimethyl-1,3-dioxan-5-one Using the SAMP-/RAMP-Hydrazone Method

Dieter Enders* , Bernhard Bockstiegel
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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The lithiated SAMP-hydrazone (S)-3 [(S)-1-(2,2-dimethyl-1, 3-dioxan-5-ylideneamino)-2-methoxymethylpyrrolidine] is used as a chiral 1,3-dihydroxyacetone-enolate equivalent C in overall enantioselective α-alkylations leading to 4-alkyl-2,2-dimethyl-1,3-dioxan-5-ones (S)-5a-i in good overall chemical yields and of high enantiomeric purity (ee = 88 - ≧ 93%.