Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

Abstract

The asymmetric cycloaddition of TIPS nitronate catalyzed by “Cu(II)-bisoxazoline” gave the 2-isoxazoline product in 95% yield, which was converted into tert-butyl (3S,5R)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate in 14 steps through a β-hydroxy ketone.

Keywords

• β-hydroxy ketone
• cycloaddition
• 1,3-diol
• isoxazoline
• silyl nitronate