Stereoretentive Catalytic [3+2]-Cycloaddition/Rearrangement/Decarboxylation Reactions of Indoles with Non-Racemic Donor–Acceptor Cyclopropanes
Stereoretentive Catalytic [3+2]-Cycloaddition/Rearrangement/Decarboxylation Reactions of Indoles with Non-Racemic Donor–Acceptor Cyclopropanes
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DOI：
10.1021/acscatal.2c05930
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发表时间：
2023-01
期刊：
影响因子：
12.9
通讯作者：
M. Bao;K. Lopez;Rajesh Gurung;Hadi D Arman;M. Doyle
中科院分区：
文献类型：
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作者：
M. Bao;K. Lopez;Rajesh Gurung;Hadi D Arman;M. Doyle
以高氯酸镍（II）和三氟甲磺酸钪（III）为催化剂，依次与3-甲基吲哚和非外消旋的给体-受体环丙烷进行“一锅法”环戊环加成-重排级联反应，在温和的反应条件下，以高产率和对映体保留率合成了手性二氢-3H-咔唑-2-羧酸酯衍生物.高度非对映选择性的[3+2]-环加成依赖于3-甲基吲哚取代基。此外，这些二氢-3H-咔唑-2-羧酸酯在出乎意料的温和反应条件下通过水解和脱羧的进一步转化提供了以中等产率直接获得脱羧化合物的方法，并具有高的对映体纯度保留。
A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is reportedviaa “one-pot” cyclopentannulation-rearrangement cascade reaction that is sequentially catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate with 3-methylindole and non-racemic donor–acceptor cyclopropanes in high yields and enantioretention under mild reaction conditions. Highly diastereoselective [3+2]-cycloaddition is dependent on 3-methylindole substituents. In addition, a further transformation of these dihydro-3H-carbazole-2-carboxylatesviahydrolysis and decarboxylation under unexpectedly mild reaction conditions provides straightforward access to the decarboxylated compounds in moderate yields with high retention of enantiomeric purity.