Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine

Aziridine Epimer Conjugate Stereoisomerism Natural product
DOI: 10.1039/c3ob27390c Publication Date: 2013-02-26T09:40:53Z
ABSTRACT
Polyhydroxylated pyrrolidines, such as biologically important azafuranoses represented by the natural product (+)-2,5-imino-2,5,6-trideoxy-gulo-heptitol and its C(3)-epimer, were elaborated from a commercially available enantiomerically pure (2R)-hydroxymethylaziridine highly stereoselective directed reactions in more than 61% overall yield. At first, nucleophile 2-trimethylsilyloxyfuran was to (2R)-aziridine-2-carboxaldehyde ZnBr2 yield unusual anti-addition single isomer via chelation-controlled transition. The ring opening of aziridine followed conjugate addition give cis-fused bicycle, which converted target molecule after required reductive operations.
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