Reactivity of cyclopropanic δ-oxo-α,β-unsaturated esters towards SmI2: 3-exo-trig cyclisation versus cyclopropane ring opening
作者： Chama Cammoun , Riadh Zriba , Sophie Bezzenine-Lafollée , François Guibé
DOI: 10.1016/J.TET.2007.02.080
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摘要: Abstract trans -(2′,2′-Diphenyl-bicyclopropyl-2-yl)-4,4-dimethyl-5-oxo-pent-2-enoic acid methyl ester 9 , undergoes 3- exo - trig cyclisation in the presence of SmI 2 without competitive ring opening Newcomb's bicyclopropylic probe next to carbonyl group. From this result, it may be concluded that absence observed earlier case 5-cyclopropyl-4,4-dimethyl-5-oxo-pent-2-enoate 7 is not due potentially reversible character process. Meanwhile, as deduced from kinetic considerations based on data literature, does necessarily mean formation ketyl radicals involved cyclisations δ-oxo-α,β-unsaturated esters. Compounds and cyclise with total syn selectivity, leading ultimately lactones. This selectivity contrasts other alkylic
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