Publication | Closed Access
A Highly Efficient Asymmetric Synthesis of Homotaurine Derivatives via Diastereoselective Ring-Opening of γ-Sultones
17
Citations
0
References
2004
Year
Chemical EngineeringEngineeringBiochemistryNatural SciencesDiversity-oriented Synthesisγ-Substituted γ-Amino Sulfonatesγ-Substituted γ-SultonesHomotaurine DerivativesOrganic ChemistryDiastereoselective Ring-openingChemistryStereoselective SynthesisEfficient Asymmetric SynthesisNatural Product SynthesisAsymmetric CatalysisSynthetic ChemistryEnantioselective Synthesis
A highly efficient asymmetric synthesis of α,γ-substituted γ-amino sulfonates via diastereoselective ring-opening of enantiopure α,γ-substituted γ-sultones with inversion of configuration at the attacked γ-carbon is described. In the key step sodium azide is used as the nucleophilic nitrogen source. Secondary and tertiary γ-amino sulfonates were synthesized in very good yields and excellent diastereo- and enantiomeric excesses (de, ee ≥98%).