Formal [3+2] Cycloaddition Between in situ Formed 1, 4‐Benzodiazepin‐2‐One‐Based Azomethine Ylides and Azodicarboxylic Acid Derivatives: Diastereoselective Synthesis of Spiro‐1, 4‐Benzodiazepin‐2‐Ones. Issue 5 (20th January 2021)

• Record Type: Journal Article
• Authors: Fan, Xiao‐Zu; Wu, Hui‐Hui; Tang, Zhe; Zhang, Heng; Cai, Lu‐Yu; Bi, Xiao‐Fan; Zhao, Hong‐Wu
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 5(2021)
• Page Start: 1379
• Page End: 1389
• Publication Date: 2021-01-20
• Subjects: [3+2] cycloaddition -- 1, 4-benzodiazepin-2-one-based azomethine ylide -- azodicarboxylic acid derivative -- diastereoselectivity -- spiro-1, 4-benzodiazepin-2-one; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202001486
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: In the presence of PhCO2 H (20 mol%), the formal [3+2] cycloaddition between in situ formed 1, 4‐benzodiazepin‐2‐one‐based azomethine ylides and azodicarboxylic acid derivatives proceeded readily, thus leading to the formation of trans ‐configured spiro‐1, 4‐benzodiazepin‐2‐ones in up to 98% chemical yield with >20:1 dr . The relative configuration of the title compounds was unambiguously determined by means of X‐ray single crystal structure analysis. The reaction mechanism was hypothesized to account for the diastereoselective formation of the isolated spiro‐1, 4‐benzodiazepin‐2‐ones. Abstract :