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

Title
Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
Authors
Lee H.Kim J.H.Lee W.K.Cho J.Nam W.Lee J.Ha H.-J.
Ewha Authors
남원우
SCOPUS Author ID
남원우scopus
Issue Date
2013
Journal Title
Organic and Biomolecular Chemistry
ISSN
1477-0520JCR Link
Citation
vol. 11, no. 22, pp. 3629 - 3634
Indexed
SCI; SCIE; SCOPUS WOS scopus
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 by highly stereoselective directed reactions in more than 61% overall yield. At first, the nucleophile 2-trimethylsilyloxyfuran was directed to (2R)-aziridine-2-carboxaldehyde by ZnBr2 to yield the unusual anti-addition product as a single isomer via the chelation-controlled transition. The ring opening of aziridine was followed by conjugate addition to give a cis-fused bicycle, which was converted to the target molecule after the required reductive operations. This journal is © The Royal Society of Chemistry 2013.
DOI
10.1039/c3ob27390c
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자연과학대학 > 화학·나노과학전공 > Journal papers
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