Direct Access to 3,4‐Fused Spirooxindoles Through Visible‐Light‐Driven Diasterioselective [4+2] Cyclization of 3‐Methylene Oxindoles

Abstract A visible light‐mediated strategy has been developed to synthesize diastereoselective 3,4‐fused spirooxindoles via formal [4+2] cycloaddition of 3‐methylene oxindoles without the need of pre‐functionalization. The 3‐methylene oxindoles, when exposed to visible light in the presence of catalytic amount of CeCl 3 under alkaline conditions, afforded the complex 3,4‐fused spirooxindole framework with four contiguous chiral centers. The protocol proved to be highly chemo‐ and regio‐selective by affording 3,4‐fused spirooxindoles in moderatetogood yields. The protocol also works smoothly under the direct exposure of sunlight. It has been demonstrated that the method is also scalable on gram quantity.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-04-15
DOI
https://doi.org/10.1002/ajoc.202500424
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94

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article

Direct Access to 3,4‐Fused Spirooxindoles Through Visible‐Light‐Driven Diasterioselective [4+2] Cyclization of 3‐Methylene Oxindoles

Anindita Bhowmick, Ramakrishna G. Bhat, Abhijeet S. Sabale, Onkar S. Bankar et al.
1 citations
Asian Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.94
article

Direct Access to 3,4‐Fused Spirooxindoles Through Visible‐Light‐Driven Diasterioselective [4+2] Cyclization of 3‐Methylene Oxindoles

Anindita Bhowmick, Ramakrishna G. Bhat, Abhijeet S. Sabale, Onkar S. Bankar, Sovan Pattanaik
article en
1 citations

Abstract

Abstract A visible light‐mediated strategy has been developed to synthesize diastereoselective 3,4‐fused spirooxindoles via formal [4+2] cycloaddition of 3‐methylene oxindoles without the need of pre‐functionalization. The 3‐methylene oxindoles, when exposed to visible light in the presence of catalytic amount of CeCl 3 under alkaline conditions, afforded the complex 3,4‐fused spirooxindole framework with four contiguous chiral centers. The protocol proved to be highly chemo‐ and regio‐selective by affording 3,4‐fused spirooxindoles in moderatetogood yields. The protocol also works smoothly under the direct exposure of sunlight. It has been demonstrated that the method is also scalable on gram quantity.

Asian Journal of Organic ChemistryVol. 14(7)
Indian Institute of Science Education and Research Pune (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Indian Institute of Science Education and Research Pune, Indian Institute of Science Education and Research Mohali, Science and Engineering Research Board
Openalex Percentile: Top 27%
Catalytic C–H Functionalization Methods
0.94
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