Highly efficient and diastereoselective construction of substituted pyrrolidines bearing a quaternary carbon center via 1, 3‐dipolar cycloaddition. (13th May 2022)

• Record Type: Journal Article
• Authors: Wang, Kai‐Kai; Li, Yan‐Li; Shuai, Xiao‐Qian; Chen, Rongxiang; Sun, Aili; Wang, Zhan‐Yong
• Is Part Of: Journal of heterocyclic chemistry. Volume 59:Number 9(2022)
• Page Start: 1616
• Page End: 1625
• Publication Date: 2022-05-13
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.4494
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract: A general approach to substituted pyrrolidines via [3 + 2] cycloaddition between nonstabilized azomethine ylides and cyanosulfones was developed. The efficient method provides a series of substituted pyrrolidines bearing a quaternary carbon center in high yields (up to 98%) excellent diastereoselectivities (up to >25:1 dr ) under ambient reaction conditions. Abstract : A [3 + 2] 1, 3‐dipolar cycloaddition of conjugated arylcyanosulfones with in situ‐generated non‐stabilized azomethine ylide from an N‐benzyl precursor is developed. The reactions afforded a clean and facile access to diverse substituted pyrrolidines in high yields (up to 98%) with excellent diastereoselective.