Nickel(II)‐Catalyzed Diastereo‐ and Enantioselective Michael/ Hemiacetalization Cascade Reaction of α‐Ketoesters with 2‐(2‐Nitrovinyl)phenols

• Published in: Advanced synthesis & catalysis Vol. 361; no. 19; pp. 4611 - 4622
• Main Authors: Chen, Long, Yang, Wu‐Lin, Shen, Jia‐Huan, Deng, Wei‐Ping
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 08.10.2019; Wiley Subscription Services, Inc
• Subjects: asymmetric catalysis; Cascade chemical reactions; Chemistry; Chemistry, Applied; Chemistry, Organic; chromane; Enantiomers; enantioselective cascade reaction; Nickel; Phenols; Physical Sciences; Science & Technology; α-ketoesters; nickel; CHROMANS; COMPLEX; ASYMMETRIC-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; STRATEGY; alpha-ketoesters; asymmetric catalysis; CATALYST; 3+2 CYCLOADDITION; chromane; enantioselective cascade reaction; 1,2-DICARBONYL COMPOUNDS; ACCESS; CONJUGATE ADDITION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201900753

A nickel(II)/diamine‐catalyzed diastereo‐ and enantioselective Michael/hemiacetalization cascade reaction of α‐ketoesters with 2‐(2‐nitrovinyl)phenols has been established, thus providing a range of structurally diverse polysubstituted chromanes in good yields and excellent stereoselectivities (up to 89% yield, >20:1 dr, >99% ee). Moreover, the gram‐scale experiment was performed with only 0.5 mol% of catalyst, and tricyclic furanobenzodihydropyran compound was gained by the derivatization of product, which showed the great synthetic potential of this strategy.