Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis

Abstract

A highly efficient enantioselective direct C–H functionalization of β-carbolines via a Minisci-type radical process under a photo-redox and chiral phosphoric acid cooperative catalytic system has been disclosed. Through this protocol, a wide range of C1 aminoalkylated β-carbolines were constructed directly with high levels of enantioselectivities from readily available β-carbolines and alanine-derived redox-active esters. This transformation allows straightforward access to highly valuable enantioenriched β-carbolines, which are an intriguing structural motif in valuable natural products and synthetic bio-active compounds. This protocol has been utilized as a highly efficient synthetic strategy for the concise asymmetric total synthesis of marine alkaloids eudistomin X, (+)-eudistomidin B and (+)-eudistomidin I.

Graphical abstract: Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Sep 2022
Accepted
23 Nov 2022
First published
24 Nov 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022, Advance Article

Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis

M. Luo, Y. Gu and S. Wang, Chem. Sci., 2022, Advance Article , DOI: 10.1039/D2SC05313F

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