Synthesis of (3′R,5′S)-3′-hydroxycotinine using 1,3-dipolar cycloaddition of a nitrone

To synthesize (3′R,5′S)-3′-hydroxycotinine [], the main metabolite of nicotine (), cycloaddition of C-(3-pyridyl)nitrones , , and with (2R)- and (2S)-N-(acryloyl)bornane-10,2-sultam [(2R)- and ] was examined. Among them, l-gulose-derived nitrone underwent stereoselective cycloaddition with to afford cycloadduct , which was elaborated to .