Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines

We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-08, Vol.366 (15), p.3303-3309
Main Authors: Ranga Rao, Vadithya, Shiva Prasad, Vadla, Ravi, Dharavath, Anil Kumar, Chelukalapally, Kumar Nechipadappu, Sunil, ReddyAdiyala, Praveen
Format: Article
Language:English
Subjects:
3-(2-isocyanoethyl)indoles
alkali metal salt K2S2O8
Alkali metals
Capillary flow
Capillary tubes
Cascade chemical reactions
Chemical synthesis
Continuous flow
Decarboxylation
Indoles
PFA (Perfluoroalkoxy alkane) capillary micro reactor
polycyclic spiroindolines
Potassium persulfate
Stereoselectivity
Visible-light
α-oxocarboxylic acids
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Summary:We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mild reaction conditions. This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindolines bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400406