Cover Picture: Unexpected Cascade Reactions of Ortho‐Hydroxyenaminones and β, γ‐Unsaturated α‐Ketoesters to Access Hydrogenated Benzoxazolepolycycles and Pyrrole−Phenol Atropisomers (Adv. Synth. Catal. 21/2019). Issue 21 (22nd October 2019)

• Record Type: Journal Article
• Authors: Bai, Xuguan; Wang, Lele; Zhang, Ziying; Zhang, Kuan; Bu, Zhanwei; Wu, Yufeng; Zhang, Wenjing; Wang, Qilin
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 21(2019)
• Page Start: 4838
• Page End: 4838
• Publication Date: 2019-10-22
• Subjects: cascade reaction -- benzoxazole -- axial chirality -- polycyclic heterocycle -- atropisomer; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901313
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract : The inside cover picture, designed by Xiaoyi Tong, Qilin Wang and co‐workers, illustrate an unexpected BF3 ⋅OEt2 ‐catalyzed Michael addition/cyclization/dehydration sequence of ortho ‐hydroxyenaminones with aldehyde‐derived β, γ‐unsaturated α‐ketoesters, which afforded a wide range of fused hydrogenated benzoxazole polycycles in 67‐95% yields in a highly diastereoselective manner. When isatin‐derived β, γ‐unsaturated α‐ketoesters were employed, completely different reactivities were observed, delivering an array of new atropisomers with an oxindole‐substituted N‐C axially chiral pyrrole‐phenol backbone in up to 97% yield. Details of this work can be found in the communication on pages 4893–4901 (X. Bai, L. Wang, Z. Zhang, K. Zhang, Z. Bu, Y. Wu, W. Zhang, Q. Wang, Adv. Synth. Catal . 2019, 361, 4893–4901; DOI: 10.1002/adsc.201900950 ).