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You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. Method 4: Formation of Carbonyl Ylides

DOI: 10.1055/sos-SD-029-00127

Benneche, T.Science of Synthesis, (200729182.

1,3-Dipolar reagents are important in the syntheses of five-membered heterocylic compounds by [2+3]-cycloaddition reactions.[‌172‌] 1,3-Dipolar carbonyl ylides, e.g. 288, can be prepared by the reduction of bis(α-iodoalkyl) ethers with samariumiodine[‌175‌] or a manganeselead reducing system and trapped in [2+3]-cycloaddition reactions with unsaturated compounds, e.g. to give 289 (Scheme 131).[‌176‌,‌177‌]

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