✍ Scribed by Vsevolod V. Nikolaev; Anthony Linden; Heinz Heimgartner
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Thermolysis of dimethyl 2‐[(3‐oxo‐3__H__‐isoindol‐1‐yl)oxy]malonate (8) promotes a [1,4]‐H shift in the imidic NCOCH fragment of the starting molecule, which leads to a reactive carbonyl ylide. This carbonyl ylide can be trapped by the CN bond of imidates and imines, as well as the CO bond of benzaldehyde. The corresponding cycloadducts 11, 14, and 16 are formed regioselectively in good yields (60–95%) and with high stereoselectivity. In the case of 11, the minor cycloadduct in solution undergoes an isomerization to give the more stable stereoisomer. The structures of two cycloadducts, i.e., 11a and 14a, have been established by X‐ray crystallography.
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