| Summary: | 碩士 === 國立臺灣師範大學 === 化學系 === 104 === Chapter I, a novel synthesis of halogenated bicyclic γ-lactams with four stereogenic centers is developed. Treatment of iron(II) halides with six-membered ring 2-enynamides in THF under dry air afforded halogenated bicyclic [4.3.0] γ-lactams in good yields. The key feature in this reaction involving an anti-addition of a halide ion and the iron center across the activated double bond. The reactions are procedurally simple, high yielding, and excellently diastereoselective, producing bicyclic γ-lactams under mild conditions without additional oxidizing agents.
Chapter II, an efficient synthesis of halogenated bicyclic oxazolidines with four stereogenic centers is reported. Treatment of iron(III) halides with six-membered ring 2,3-epoxy-1-ynamide in ether under nitrogen proceeds rapidly to afford halogenated bicyclic [4.3.0] oxazolidines in moderate yields. The reactions are procedurally simple, efficient and excellently diastereoselective, producing halogenated bicyclic oxazolidines under mild conditions.
|
|---|
