Journal ArticleDOI
Highly stereocontrolled synthesis of the key intermediate of 1β-methylcarbapenem antibiotic via intramolecular nitrone 1,3-dipolar cycloaddition
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TLDR
The key synthetic intermediate of 1β-methyl carbapenem antibiotic, (3S, 4R)-3-[(1R)-1-t- butyl-dimethylsiloxyethyl]-4-[(2R)-2-(1-hydroxypropyl)]azetidin-2-one (2), was synthesised from (R)-methyl 3-hydrox-2 -methylpropionate with high stereoselectivity via intramolecular nitrone 1,3-dipolar cycloaddition as mentioned in this paper.Abstract:
The key synthetic intermediate of 1β-methylcarbapenem antibiotic, (–)-(3S, 4R)-3-[(1R)-1-t- butyl-dimethylsiloxyethyl]-4-[(2R)-2-(1-hydroxypropyl)]azetidin-2-one (2), was synthesised from (R)-methyl 3-hydroxy-2-methylpropionate with high stereoselectivity via intramolecular nitrone 1,3-dipolar cycloaddition.read more
Citations
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Journal ArticleDOI
Asymmetric 1,3-Dipolar Cycloaddition Reactions
Journal ArticleDOI
Preparations of two pivotal intermediates for the synthesis of 1-β-methyl carbapenem antibiotics
Journal ArticleDOI
α-Amino acids as chiral educts for stereoselective syntheses of pyrrolidine and pyrrolizidine systems☆
Ugo Chiacchio,F. Casuscelli,Antonino Corsaro,Vito Librando,Antonio Rescifina,Roberto Romeo,Giuseppe Romeo +6 more
TL;DR: In this paper, a 1,3-dipolar cycloaddition of homochiral nitrones was used for functionalization of pyrrolidine and polypyrrolizidine.
Journal ArticleDOI
Diastereoselective Route to Novel Fused or Bridged Tricyclic β-Lactams through Intramolecular Nitrone–Alkene Cycloaddition of 2-Azetidinone-Tethered Alkenylaldehydes – Synthetic Applications to Carbacephams and Cyclic β-Amino Acid Derivatives
Benito Alcaide,Elena Sáez +1 more
TL;DR: In this article, a direct route to optically pure unusually fused or bridged tricyclic β-lactams has been developed by use of intramolecular nitrone-alkene cycloaddition (INAC) reactions of easily available monocyclic 2-azetidinone-tethered alkenylaldehydes as the key synthetic step.
Journal ArticleDOI
Stereoselective synthesis of isoxazole and pyrazole annulated sultams via intramolecular 1,3-dipolar cycloaddition reactions
Ugo Chiacchio,Antonino Corsaro,Giuseppe Gumina,Venerando Pistarà,Antonio Rescifina,Manlio Alessi,Anna Piperno,Giovanni Romeo,Roberto Romeo +8 more
TL;DR: In this paper, a functionalized isothiazoloisoxazole-4,4dioxide, pyrazoloisothiazole-1,1-dioxide and benzo[1,2]thiazoline-4.4d dioxide systems have been obtained by intramolecular 1,3-dipolar cycloaddition, starting from substituted α- and β-sulfonamides.
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