Chemo- and Regioselective Asymmetric Synthesis of Cyclic Enamides through the Catalytic Umpolung Organocascade Reaction of α‑Imino Amides

The efficient chemo- and regioselective catalytic asymmetric syntheses of enamides, which are important core structures of bioactive natural products, have been achieved through the first umpolung organocascade reaction of α-imino amides. A variety of enamides have been synthesized enantioselectivel...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (11), p.7362-7371
Main Authors: Yoshida, Yasushi, Hiroshige, Tomohiko, Omori, Kazuki, Mino, Takashi, Sakamoto, Masami
Format: Article
Language:English
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Summary:The efficient chemo- and regioselective catalytic asymmetric syntheses of enamides, which are important core structures of bioactive natural products, have been achieved through the first umpolung organocascade reaction of α-imino amides. A variety of enamides have been synthesized enantioselectively in high yields with up to 99% ee. Notably, both enantiomers of the products can be selectively prepared by the simple pretreatment of the substrate. Mechanistic studies reveal that E/Z-geometry information from the substrate is transferred to the product. The present method can be applied to a wide range of α-imino amides, irrespective of the electronic nature of the substituents.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01036