Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions
Jorin Hoogenboom1, Han Zuilhof1,2, Tom Wennekes1
1Laboratory of Organic Chemistry, Wageningen University , Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
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.
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