Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams

Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams

Optically active 4-methyl-4-carbomethoxy-Δ2-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction pro...

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Veröffentlicht in:Journal of organic chemistry 1997-05, Vol.62 (11), p.3586-3591
Hauptverfasser: Hsiao, Yi, Hegedus, Louis S
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container_title Journal of organic chemistry
container_volume 62
creator Hsiao, Yi
Hegedus, Louis S
description Optically active 4-methyl-4-carbomethoxy-Δ2-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.
doi_str_mv 10.1021/jo962343e
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title Synthesis of Optically Active Imidazolines, Azapenams, Dioxocyclams, and Bis-dioxocyclams
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