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

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 t...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-10, Vol.361 (19), p.4611-4622
Hauptverfasser: Chen, Long, Yang, Wu‐Lin, Shen, Jia‐Huan, Deng, Wei‐Ping
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Sprache:eng
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Zusammenfassung: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900753