title: Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones.
abstract: Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with L-gulose-derived chiral nitrones in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. The selectivity was strongly influenced by the bulkiness of the C-substituent of the nitrone: for example, C-benzyloxymethyl nitrone afforded four stereoisomers, whereas bulky C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]nitrone gave a single stereoisomer. The latter product was elaborated to afford key synthetic intermediates for polyoxin C and dysiherbaine.
authors: Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan. tamura@ac.shoyaku.ac.jp
authors: Osamu
authors: O
authors: Tamura
authors: Kodai
authors: K
authors: Takeda
authors: Naka
authors: N
authors: Mita
authors: Masanori
authors: M
authors: Sakamoto
authors: Iwao
authors: I
authors: Okamoto
authors: Nobuyoshi
authors: N
authors: Morita
authors: Hiroyuki
authors: H
authors: Ishibashi
mesh_terms: D005663:Furans / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C454640:2-trimethylsilyloxyfuran; D005663:Furans; D006601:Hexoses; D009589:Nitrogen Oxides; C015388:nitrones; C057406:gulose