Abstract
Diverse substituted isoxazolidines 2–4 are assembled on solid phase by condensing hydroxylamines with aldehydes and trapping the resulting nitrones with various dipolarophiles. The one-pot three-component cycloaddition reaction yields the isoxazolidines in good to excellent yield. Three different reaction pathways - each dealing with one of the three components attached to the solid support - are evaluated with respect to versatility and yield of the synthesized isoxazolidines. Structures and relative configurations of representative isoxazolidines are elucidated with 1H-NMR, TOCSY, HSQC and NOESY. The reaction of polymer-bound hydroxylamines with aldehydes and alkenes is found to be the most successful. The kinetics of the solid phase reaction are determined by FT-IR-ATR spectroscopy. Polymer-bound nitrones are stable for the split/combine synthesis. A library of isoxazolidines is synthesized by the split/combine method and analyzed by means of HPLC-MS.
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