title: Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine.
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.
authors.affiliation: Department of Chemistry, Sogang University, Seoul 121-742, Korea.
authors.forename: Hogyu
authors.initials: H
authors.lastname: Lee
authors.forename: Jun Hee
authors.initials: JH
authors.lastname: Kim
authors.forename: Won Koo
authors.initials: WK
authors.lastname: Lee
authors.forename: Jaeheung
authors.initials: J
authors.lastname: Cho
authors.forename: Wonwoo
authors.initials: W
authors.lastname: Nam
authors.forename: Jaedeok
authors.initials: J
authors.lastname: Lee
authors.forename: Hyun-Joon
authors.initials: HJ
authors.lastname: Ha
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D008958:Models, Molecular; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C454640:2-trimethylsilyloxyfuran; D001372:Aza Compounds; D001388:Aziridines; D001688:Biological Products; D005663:Furans; D011759:Pyrrolidines; D013402:Sugar Alcohols; C033132:aziridine