Catalytic Asymmetric Interrupted Nazarov-Type Cyclization of 2-Indolylmethanols with Cyclic Enaminones
Catalytic Asymmetric Interrupted Nazarov-Type Cyclization of 2-Indolylmethanols with Cyclic Enaminones
复制标题
2-吲哚甲醇与环烯胺催化不对称间断纳扎罗夫型环化
DOI：
10.1039/c8ob01427b
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发表时间：
2018
影响因子：
3.2
通讯作者：
Feng Shi
中科院分区：
文献类型：
--
作者：
Jia-Le Wu;Cong-Shuai Wang;Jin-Rong Wang;Guang-Jian Mei;Feng Shi
以环烯胺酮为亲核试剂，建立了手性磷酸催化的C3-烯基取代的2-吲哚甲醇的不对称间断纳扎罗夫型环化反应，得到了具有优异非对映选择性和中等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催化不对称转化的研究内容，而且推动了催化不对称间断纳扎罗夫型环化反应的化学进展。此外，该反应也将为合成手性环戊[b]吲哚衍生物提供一种有用的方法。
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.