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Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
- Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
- 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
- Organic and Biomolecular Chemistry, 11(22), 3629-3634
- Article Type
- Conjugate Addition; Efficient Synthesis; Ionic Liquids; Natural Products; Polyhydroxylated; Ring Opening; Single-Isomer; Stereo-Selective; Stereochemistry; Stereoselectivity; Target Molecule
- 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.
- Royal Society of Chemistry
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