A non-diazo approach to functionalized (2-furyl)-2-pyrrolidines through a cascade reaction of enynal-derived zinc carbenoids with β-arylaminoketones
Literature Information
Publication Date
2023-10-12
DOI
10.1039/D3QO01354E
Impact Factor
5.281
Authors
Chenxin Ou, Bidhan Ghosh, Indrajeet Sharma
View Original
Abstract
This study introduces a cascade approach for synthesizing functionalized (2-furyl)-2-pyrrolidines, showcasing both convergence and remarkable stereoselectivity. This domino process proceeds through an N–H insertion into an enynal-derived metal–carbenoid, followed by an intramolecular aldol reaction to provide pyrrolidines with high diastereoselectivity (98 : 2). This chemistry utilizes Earth-abundant zinc chloride as a catalyst with loading as low as 1 mol%. This method operates under mild conditions and demonstrates high chemoselectivity by accommodating substrates bearing functionalities such as free alcohols, alkenes, and alkynes.
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Source Journal
Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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