Cooperative Silver‐ and Base‐Catalyzed Diastereoselective Cycloaddition of Nitrones with Methylene Isocyanides: Access to 2‐Imidazolinones. Issue 23 (14th May 2020)

• Record Type: Journal Article
• Authors: Chen, Yan; Wu, Yijing; Shatskiy, Andrey; Kan, Yuhe; Kärkäs, Markus D.; Liu, Jian‐Quan; Wang, Xiang‐Shan
• Is Part Of: European journal of organic chemistry. Issue 23(2020)
• Page Start: 3475
• Page End: 3479
• Publication Date: 2020-05-14
• Subjects: Diastereoselectivity -- Imidazolinones -- Isocyanides -- Nitrones -- Silver; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000437
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A protocol involving cooperative silver‐ and base‐catalyzed diastereoselective cycloaddition of nitrones with isocyanides is described, providing access to a wide range of 2‐imidazolinone derivatives with various functional groups as single diastereomers. Varying the base and temperature of the reaction allowed selective access to both diastereomers of the product. A plausible reaction mechanism is proposed and supported by DFT calculations. Abstract : A protocol involving cooperative silver‐ and base‐catalyzed diastereoselective cycloaddition of nitrones with isocyanides is described, delivering several valuable 2‐imidazolinones derivatives as single diastereomers. A plausible reaction mechanism is rationalized by DFT calculations. DBU plays dual roles in the developed reaction, acting as both the base and ligand.