Issue 17, 2024

Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Abstract

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols with 3-substituted-2-indolylmethanols was conducted in the presence of chiral phosphoric acids, which delivered a series of chiral pyrrolo[1,2-α]indoles in overall high yields (up to 98%) with excellent diastereoselectivities (all >95 : 5 dr) and good enantioselectivities (up to 94% ee). Moreover, theoretical calculations provided an in-depth understanding of the reaction pathways. This work not only establishes the first catalytic asymmetric cycloaddition of methyl-substituted 2-indolylmethanols, but also realizes the first catalytic asymmetric formal (2 + 3) cycloaddition between different 2-indolylmethanols, which will enrich the chemistry of indolylmethanols.

Graphical abstract: Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jun 2024
Accepted
08 Jul 2024
First published
08 Jul 2024

Org. Chem. Front., 2024,11, 4812-4819

Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

S. Liu, T. Li, N. Wang, Q. Cheng, Y. Jiao, Y. Zhang and F. Shi, Org. Chem. Front., 2024, 11, 4812 DOI: 10.1039/D4QO01047G

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