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Asymmetric Cascade Aza-Henry/Lactamization Reaction in the Highly Enantioselective Organocatalytic Synthesis of 3-(Nitromethyl)isoindolin-1-ones from α-Amido Sulfones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-14 , DOI: 10.1021/acs.joc.2c00518
Lorenzo Serusi 1 , Laura Palombi 2 , Giovanni Pierri 1 , Antonia Di Mola 1 , Antonio Massa 1
Affiliation  

The asymmetric synthesis of novel 3-substituted isoindolinones is herein reported. A new cascade reaction was developed that consisted of the asymmetric nitro-Mannich reaction of suitable α-amido sulfones designed from 2-formyl benzoates, followed by the in situ cyclization of the adducts. Very high enantioselectivities, up to 98% ee, and very good yields were obtained in the presence of the readily available neutral bifunctional organocatalyst derived from trans-1,2-diaminocyclohexane, which is known as Takemoto’s catalyst. The investigation of the reactivity of the obtained products allowed either the selective Boc-deprotection or reduction of the nitro group, leading to further functionalized 3-substituted isoindolinones without affecting the enantiomeric purity.

中文翻译:

α-氨基砜高对映选择性有机催化合成 3-(硝基甲基)异吲哚啉-1-酮的不对称级联氮杂-亨利/内酰胺化反应

本文报道了新型 3-取代异吲哚啉酮的不对称合成。开发了一种新的级联反应,该反应包括由 2-甲酰苯甲酸酯设计的合适的 α-酰胺基砜的不对称硝基-曼尼希反应,然后加合物的原位环化。在容易获得的衍生自反-1,2-二氨基环己烷的中性双功能有机催化剂(被称为 Takemoto 催化剂)的存在下,获得了非常高的对映选择性,高达 98% ee 和非常好的产率。对所得产物反应性的研究允许选择性 Boc 去保护或还原硝基,从而在不影响对映体纯度的情况下进一步官能化 3-取代的异吲哚啉酮。
更新日期:2022-06-14
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