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Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Tetrahedron ( IF 2.1 ) Pub Date : 2019-12-18 , DOI: 10.1016/j.tet.2019.130883
Jae Won Yoo , Youngran Seo , Jong Beom Park , Young Gyu Kim

Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.



中文翻译:

脂族醛的双向同系化:通过相同的中间体进行一碳的缩短和延长

脂肪醛可通过相同的中间体β,γ-不饱和α-硝基砜,经脯氨酸催化的连续反应制备的相同中间体,通过2–4个反应,与一碳短和一碳长的同源羰基化合物同源。几种脂肪醛与苯磺酰基硝基甲烷。当关键中间体的氧化裂解得到一碳较少的同源羰基化合物时,相同关键中间体的还原随后被氧化产生了更多一碳的同源羰基化合物。

更新日期:2019-12-19
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