Enantioselective Synthesis of Spirorhodanine-Pyran Derivatives via Organocatalytic [3 + 3] Annulation Reactions between Pyrazolones and Rhodanine-Derived Ketoesters.,Organic Letters

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Enantioselective Synthesis of Spirorhodanine-Pyran Derivatives via Organocatalytic [3 + 3] Annulation Reactions between Pyrazolones and Rhodanine-Derived Ketoesters.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-15 , DOI: 10.1021/acs.orglett.9b04571
Dong-Sheng Ji ₁ , Yong-Chun Luo ₁ , Xiu-Qin Hu ₁ , Peng-Fei Xu ₁

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A series of novel biselectrophilic β,γ-unsaturated α-ketoesters were designed and synthesized from rhodanine. Under the catalysis of chiral squaramides, the enantioselective [3 + 3] annulation reaction of these novel ketoesters with pyrazolones was developed. This reaction offers an efficient method for the synthesis of chiral 2'-thioxo-5,6-dihydrospiro[pyrano[2,3-c]pyrazole-4,5'-thiazolidin]-4'-ones.

中文翻译：

通过吡唑啉酮与若丹宁衍生的酮酸酯之间的有机催化[3 + 3]环合反应对映体合成吡咯烷丹宁-吡喃衍生物。

由若丹宁设计合成了一系列新型的双亲电子的β，γ-不饱和α-酮酸酯。在手性方酰胺的催化下，开发了这些新型酮酯与吡唑啉酮的对映体选择性[3 + 3]环化反应。该反应提供了一种有效的手性2'-thioxo-5,6-dihydrospiro [pyrano [2,3-c] pyrazole-4,5'-thiazolidin] -4'-ones的合成方法。

更新日期：2020-01-15

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