A Chitosan-CatalyzedDomino Aldol-Hetero-Diels-Alder Synthesis of Cyclic Heptanoid-Annulated Pyran Scaffolds,ChemistrySelect

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A Chitosan-CatalyzedDomino Aldol-Hetero-Diels-Alder Synthesis of Cyclic Heptanoid-Annulated Pyran Scaffolds
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-11-25 , DOI: 10.1002/slct.202103333
Hiralben D. Atara ₁ , Gaurangkumar C. Brahmbhatt ₁ , Vishalkumar M. Parmar ₁ , Narsidas J. Parmar ₁ , Vivek K. Gupta ₂

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The biopolymer chitosan has been demonstrated as a highly efficient heterogeneous catalyst to promote the DAHDA reaction.Where poorly enolizable CH activated methyl ketone unitswere reacted with olefin-tethered aldehydes in glycerol medium to achieve new cyclic heptanoid-incorporated poly heterocycles. The reaction is diastereoselective in that the E-aldol intermediate leads the formation of cis-fused products via endo-E-syn transition state. E-factor (0.15) and EcoScale (77.5 %) values of the method to afford product 5 aa are key green aspects of the protocol.

中文翻译：

壳聚糖催化多米诺羟醛-杂-Diels-Alder 合成环状庚烷环化吡喃支架

生物聚合物壳聚糖已被证明是一种促进 DAHDA 反应的高效多相催化剂。其中，烯醇化差的 CH 活化的甲基酮单元在甘油介质中与烯烃系醛反应，以实现新的环状庚烷结合多杂环。该反应是非对映选择性的，因为 E-羟醛中间体通过内-E- syn 过渡态导致顺式融合产物的形成。提供产品5 aa的方法的 E 因子 (0.15) 和 EcoScale (77.5%) 值是该协议的关键绿色方面。

更新日期：2021-11-25

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