title: A practical preparation of the key intermediate for penems and carbapenems synthesis.
abstract: A novel, practical and stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, a key intermediate in the preparation of β-lactam antibiotics is reported. The crucial step of the synthesis is based on the Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade between silyl protected (R)-3-butyn-2-ol and the nitrone derived from benzyl hydroxylamine and benzyl glyoxylate. The obtained adduct is subjected to debenzylation with sodium, or lithium in liquid ammonia followed by oxidation with lead tetraacetate to afford the final product.
authors.affiliation: Institute of Organic Chemistry of Polish Academy of Sciences, Warsaw, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Grzeszczyk
authors.forename: Sebastian
authors.initials: S
authors.lastname: Stecko
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Mucha
authors.forename: Olga
authors.initials: O
authors.lastname: Staszewska-Krajewska
authors.forename: Marek
authors.initials: M
authors.lastname: Chmielewski
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Furman
mesh_terms: D000641:Ammonia / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D012964:Sodium / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C110742:4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone; D000900:Anti-Bacterial Agents; D015780:Carbapenems; D007769:Lactams; D009942:Organometallic Compounds; D047090:beta-Lactams; D000641:Ammonia; D008094:Lithium; D012964:Sodium; C029433:lead tetraacetate