Cited 6 time in webofscience Cited 8 time in scopus

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[Lee, Hogyu]Kim, JH[Kim, Jun Hee]Lee, WK[Lee, Won Koo]Cho, J[Cho, Jaeheung]Nam, W[Nam, Wonwoo]Lee, J[Lee, Jaedeok]Ha, HJ[Ha, Hyun-Joon]
DGIST Authors
Cho, J[Cho, Jaeheung]
Issue Date
2013
Citation
Organic and Biomolecular Chemistry, 11(22), 3629-3634
Type
Article
Article Type
Article
Keywords
Conjugate AdditionEfficient SynthesisIonic LiquidsNatural ProductsPolyhydroxylatedRing OpeningSingle-IsomerStereo-SelectiveStereochemistryStereoselectivityTarget Molecule
ISSN
1477-0520
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. © The Royal Society of Chemistry 2013.
URI
http://hdl.handle.net/20.500.11750/3300
DOI
10.1039/c3ob27390c
Publisher
Royal Society of Chemistry
Files:
There are no files associated with this item.
Collection:
Emerging Materials ScienceETC1. Journal Articles


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