title: Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions.
abstract: A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University , Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
authors.forename: Jorin
authors.initials: J
authors.lastname: Hoogenboom
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University , Dreijenplein 8, 6703 HB Wageningen, The Netherlands.|Department of Chemical and Materials Engineering, King Abdulaziz University , Jeddah, Saudi Arabia.
authors.forename: Han
authors.initials: H
authors.lastname: Zuilhof
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University , Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
authors.forename: Tom
authors.initials: T
authors.lastname: Wennekes
mesh_terms: D000080:Acetals; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines; D003500:Cyclization; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000447:Aldehydes; D000588:Amines; D007555:Isoxazoles; D009589:Nitrogen Oxides; C015388:nitrones