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Synthesis 2004(17): 2910-2918
DOI: 10.1055/s-2004-831256
DOI: 10.1055/s-2004-831256
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Highly Efficient Asymmetric Synthesis of Homotaurine Derivatives via Diastereoselective Ring-Opening of γ-Sultones
Weitere Informationen
Received
23 July 2004
Publikationsdatum:
07. Oktober 2004 (online)
Publikationsverlauf
Publikationsdatum:
07. Oktober 2004 (online)
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Abstract
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%).
Key words
amino sulfonates - sultones - asymmetric synthesis - ring-opening - azide
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