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Synlett 2000; 2000(10): 1408-1410
DOI: 10.1055/s-2000-7638
DOI: 10.1055/s-2000-7638
letter
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The Synthesis of Chiral Polyhydroxylated Pyrrolidines Using a Reverse-Cope Cyclisation
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)

Ring opening of (2S,3R)-1,2-epoxy-4-penten-3-ol with N-benzylhydroxylamine hydrochloride and NaOMe in methanol gives the amine oxide (9) as a single diastereoisomer in 72% yield. Catalytic hydrogenation furnishes the parent homochiral pyrrolidine (10) in quantitative yield.
pyrrolidines - asymmetric synthesis - cyclisation - hydroxylamine - reverse-Cope