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

• Published in: European Journal of Organic Chemistry Vol. 2008; no. 23; pp. 3991 - 4003
• Main Authors: Prazeres, Verónica F. V., Castedo, Luis, González-Bello, Concepción
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-08-2008; WILEY‐VCH Verlag
• Subjects: (-)-Quinic acid; Click chemistry; Cyclic γ-amino acids; Regioselectivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200800480

Four 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)
The synthesis of polyhydroxylated γ‐azido and γ‐amino acids from (–)‐quinic acid is described. The reactivity of highly functionalized azides 2 and 4a with alkynes by click chemistry has been explored and is demonstrated in the cases of triazoles 5 and 6.