Zinc‐Catalyzed Enantioselective Dearomative [3+2] Cycloaddition Reaction of 3‐Nitrobenzothiophenes and 3‐Nitrothieno[2,3‐b]yridine with 3‐Isothiocyanato Oxindoles

• Published in: Advanced synthesis & catalysis Vol. 360; no. 7; pp. 1420 - 1425
• Main Authors: Yue, Deng‐Feng, Zhao, Jian‐Qiang, Chen, Yong‐Zheng, Zhang, Xiao‐Mei, Xu, Xiao‐Ying, Yuan, Wei‐Cheng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 03.04.2018; Wiley Subscription Services, Inc
• Subjects: 3-Isothiocyanato oxindoles; 3-Nitrobenzothiophenes; 3-Nitrothieno[2,3-b]; Asymmetric catalysis; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Cycloaddition; Heterocyclic compounds; Physical Sciences; Science & Technology; Zinc; NAPHTHOLS; ASYMMETRIC DEAROMATIZATION; 3-Isothiocyanato oxindoles; 3-b; EFFICIENT SYNTHESIS; POLYCYCLIC SPIROOXINDOLES; Asymmetric catalysis; 3-Nitrobenzothiophenes; AROMATIC-COMPOUNDS; INDOLES; CASCADE REACTION; Cycloaddition; 3-Nitrothieno; AZOMETHINE YLIDE; 3-NITROINDOLES; DERIVATIVES
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201701557

A highly diastereo‐ and enantioselective dearomative [3+2] cycloaddition reaction of 3‐nitrobenzothiophenes and 3‐nitrothieno[2,3‐b]with 3‐isothiocyanato oxindoles is developed. The reaction is catalyzed by the chiral Zn(OTf)2/bis(oxazoline, and is the second example of a catalytic asymmetric dearomative cycloaddition reaction of 3‐nitrobenzothiophene derivatives. A range of complex heterocyclic compounds containing three contiguous stereocenters, one of which is spirocyclic center, can be obtained in quantitative yields with excellent stereoselectivities.