Diastereo- and enantioselective construction of chiral cyclopenta[b]indole framework via a catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols?

Organic Chemistry Frontiers Pub Date: 2018-02-19 DOI: 10.1039/C8QO00014J

Abstract

A catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols has been established in the presence of chiral phosphoric acids, which constructed chiral cyclopenta[b]indole frameworks in generally good yields (up to 90%), high diastereoselectivities (up to >95?:?5 dr) and excellent enantioselectivities (up to 96% ee). This reaction not only provides an easy access to chiral cyclopenta[b]indole scaffolds, but also advances the chemistry of indolylmethanols, especially catalytic asymmetric transformations of indolylmethanols.

Graphical abstract: Diastereo- and enantioselective construction of chiral cyclopenta[b]indole framework via a catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols
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