Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions

Jorin Hoogenboom, Han Zuilhof, Tom Wennekes*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review


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.

Original languageEnglish
Pages (from-to)5550-5553
Number of pages4
JournalOrganic Letters
Issue number22
Publication statusPublished - 20 Nov 2015
Externally publishedYes


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