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Synlett 1995; 1995(1): 71-73
DOI: 10.1055/s-1995-4854
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Diastereoselective Addition of Organometallic Reagents to Nor-Ephedrine-Derived 2-Acyl-N-Tosyl-Oxazolidines

Giovanni Poli* , Elisa Maccagni, Leonardo Manzoni, Tullio Pilati, Carlo Scolastico
  • *Dipartimento di Chimica Organica dell’Università di Firenze, Centro CNR per lo Studio dei Composti Eterociclici, Via Gino Capponi 9, 50121, Firenze, Italy
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Publication Date:
31 December 2000 (online)

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Addition of carbanionic reagents to the 2-acyl-N-tosyl-oxazolidines 1 and 11 has been studied. Organolithium and organomagnesium reagents add to the methyl ketone 1 with remarkable Re and Si π-face selectivity respectively. With phenyl ketone 11 only organomagnesium reagents follow the above trend. Models accounting for the observed stereochemical behavior are proposed.

oxazolidines - nor-ephedrine - organometallic reagents - Cram’s rule

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