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

A highly efficient enantioselective direct C-H functionalization of beta-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 beta-carbolines were constru...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 14; no. 2; pp. 251 - 256
Main Authors Luo, Mu-Peng, Gu, Yi-Jie, Wang, Shou-Guo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.01.2023
Royal Society of Chemistry
Subjects
Alanine
Chemistry
Chemistry, Multidisciplinary
Enantiomers
Esters
Natural products
Phosphoric acid
Physical Sciences
Science & Technology
EUDISTOMIN-X
ALKALOIDS
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Summary:A highly efficient enantioselective direct C-H functionalization of beta-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 beta-carbolines were constructed directly with high levels of enantioselectivities from readily available beta-carbolines and alanine-derived redox-active esters. This transformation allows straightforward access to highly valuable enantioenriched beta-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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc05313f