Publication: [2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones
[2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones
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Mlostoń, G., Linden, A., & Heimgartner, H. (1998). [2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones. Helvetica Chimica Acta, 81(3–4), 558–569. https://doi.org/10.1002/hlca.19980810309
Abstract
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Abstract
Thermal reactions of 1,2,3-trisubstituted ariridines 1 with 1,3-thiazole-5(4H)-thiones 6 in toluene yielded, in general, a mixture of two diastereoisomeric spirocyclic [2+3] cycloadducts. The formation of these products can be explained by a stereoselective electrocyclic ring opening of 1 to give an azomethine ylide 2 as the reactive intermediate, which is trapped immediately by 6 via a stereoselective 1,3-dipolar cycloaddition. Only in the case of trans-dimethyl 1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-la), four diastere
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- Mlostoń, Grzegorz
- Heimgartner, Heinz
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Citations
Mlostoń, G., Linden, A., & Heimgartner, H. (1998). [2+3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones. Helvetica Chimica Acta, 81(3–4), 558–569. https://doi.org/10.1002/hlca.19980810309
