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A catalytic asymmetric interrupted Nazarov-type cyclization of 2-indolylmethanols with cyclic enaminones

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Abstract

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.

Graphical abstract: A catalytic asymmetric interrupted Nazarov-type cyclization of 2-indolylmethanols with cyclic enaminones

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Publication details

The article was received on 16 Jun 2018, accepted on 07 Jul 2018 and first published on 09 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01427B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    A catalytic asymmetric interrupted Nazarov-type cyclization of 2-indolylmethanols with cyclic enaminones

    J. Wu, C. Wang, J. Wang, G. Mei and F. Shi, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01427B

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