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A catalytic asymmetric interrupted Nazarov-type cyclization of 2-indolylmethanols with cyclic enaminones†
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2018-07-09 00:00:00 , DOI: 10.1039/c8ob01427b
Jia-Le Wu 1, 2, 3, 4 , Cong-Shuai Wang 1, 2, 3, 4 , Jin-Rong Wang 1, 2, 3, 4 , Guang-Jian Mei 1, 2, 3, 4 , Feng Shi 1, 2, 3, 4
Affiliation  

A chiral phosphoric acid-catalyzed asymmetric interrupted Nazarov-type cyclization of C3-alkenyl-substituted 2-indolylmethanols has been established by using cyclic enaminones as nucleophiles, which afforded chiral cyclopenta[b]indole derivatives with excellent diastereoselectivities and moderate to good enantioselectivities. This reaction will not only enrich the research contents of indolylmethanol-involved catalytic asymmetric transformations, but also advance the chemistry of catalytic asymmetric interrupted Nazarov-type cyclizations. In addition, this reaction will also provide a useful method for synthesizing chiral cyclopenta[b]indole derivatives.

中文翻译:

带有环烯胺酮的2-吲哚基甲醇催化不对称间断Nazarov型环化

通过使用环状烯胺酮作为亲核试剂,建立了手性磷酸催化的C3-烯基取代的2-吲哚基甲醇的不对称间断Nazarov型环化反应,它提供了具有优异的非对映选择性和中度至良好对映选择性的手性环戊[ b ]吲哚衍生物。该反应不仅丰富了吲哚甲醇反应所涉及的催化不对称转化的研究内容,而且还促进了催化不对称中断的Nazarov型环化反应的化学反应。另外,该反应还将提供合成手性环戊[b]吲哚衍生物的有用方法。
更新日期:2018-07-09
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