title: Highly diastereoselective conjugate addition of nitroalkanes to α,β-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones.
abstract: A series of 4,5-substituted chiral γ-lactams were synthesized through a highly diastereoselective addition-rearrangement approach from 2,3-unsaturated sugar lactones. The single-crystal X-ray structure of one product indicated that the sugar ring was attacked from the axial side. Partial reduction of the nitro group produced N-hydroxy-γ-lactams, which were further reduced with TiCl(3) to yield the 4,5-substituted chiral γ-lactams. The absolute configuration of C5 of the γ-lactam was determined by NOESY spectra.
authors: Department of Chemical Biology, Peking University, Beijing, China.
authors: Yan-Ping
authors: YP
authors: Li
authors: Zhong-Jun
authors: ZJ
authors: Li
authors: Xiang-Bao
authors: XB
authors: Meng
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D007783:Lactones; D009574:Nitro Compounds; D011760:Pyrrolidinones