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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)
Author(s) -
Bai Xuguan,
Wang Lele,
Zhang Ziying,
Zhang Kuan,
Bu Zhanwei,
Wu Yufeng,
Zhang Wenjing,
Wang Qilin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901313
Subject(s) - chemistry , atropisomer , pyrrole , phenol , yield (engineering) , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy
The inside cover picture , designed by Xiaoyi Tong, Qilin Wang and co‐workers, illustrate an unexpected BF 3 ⋅OEt 2 ‐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).