Stereoselective Synthesis of Novel Cyclic γ‐Amino Acids and Triazole Derivatives

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AbstractFour polyhydroxylated γ‐azido and three γ‐amino acids 1–4 have been synthesized from (–)‐quinic acid. The nitrogen functionality in the reported derivatives was introduced through regioselective ring‐opening of cyclic sulfates with azide anion. The synthesis of the 4‐ and 5‐epimers of γ‐azido acid 1a – derivatives 2 and 3a, respectively – was achieved by regioselective oxidation of dibutylstannylene acetals derived from 1,2‐diols, followed by diastereoselective reduction of their corresponding α‐hydroxy ketones. The presence of the azide functional group in the reported γ‐azido acids was exploited to permit interlinking of bioactive molecular entities.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)