Chemistry - A European Journal · 1995 · 25 citations · 23 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAmino Acid-derived Natural ProductsHeterocycle SynthesisAmino Acid Precursor PathwaysAsymmetric SynthesisBuilding Block MethodologyChiral Resolution Of Amino AcidsEnantioselective Synthesis
Abstract Optically active tert ‐leucinol is an important building block in asymmetric synthesis. However, the ( R ) enantiomer particularly has so far remained difficult to obtain, mainly because of the laborious synthesis of the precursor amino acid, ( R )‐ tert ‐leucine. Here we present a new, classical resolution of racemic tert ‐leucinol, which allows straightforward preparation of each, but especially the ( R ) enantiomer, in good yields and high optical purities. The feasibility of the synthesis of useful derivatives is demonstrated by transformation into the corresponding ( R )‐4‐ tert ‐butyl‐2‐oxazolidinone.
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A convenient reduction of amino acids and their derivatives
Marc J. McKennon, A. I. MEYERS, Karlheinz Drauz et al. · The Journal of Organic Chemistry · 1993 · 502 citations