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Updated: May 9, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Photoredox-Catalyzed Radical-Polar Crossover Annulation To Access Silyl/Aryl/Alkyl-Substituted N-Aryl γ-Lactams
Raghunath Chowdhury1,2, Akhil K Dubey1, Pooja Goyal1,2
1Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India.
Abstract:
A catalytic radical-polar crossover annulation reaction between N-arylglycines and β-silylmethylene malonates/aryl/alkylidene malonates under photoredox conditions has been developed. This one-pot protocol offers rapid access to silyl-substituted N-aryl γ-lactams and aryl/alkyl-substituted N-aryl γ-lactams in good to excellent yields and diastereoselectivities under mild conditions. The potentiality of this method has been demonstrated in expedient synthesis of pharmaceutical drugs such as (±)-oxiracetam, (±)-phenotropil, (±)-phenibut.HCl, and (±)-pregabalin.
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