Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols
作者： Simon B. Bedford , Kathryn E. Bell , Frank Bennett , Christopher J. Hayes , David W. Knight
DOI: 10.1039/A902411E
关键词: Sodium 、 Acetonitrile 、 Stereoselectivity 、 Chemistry 、 Azide 、 Anhydrous 、 Organic chemistry
摘要: Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range substitution patterns, leading to β-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile the presence sodium hydrogen carbonate. Such cyclizations, which not exceptions Baldwin’s rules as they electrophile-driven, appear proceed via well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy azide groups.
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