Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc02112g Click here for additional data file.

نویسندگان

  • Xiao-Dong Zuo
  • Shu-Min Guo
  • Rui Yang
  • Jian-Hua Xie
  • Qi-Lin Zhou
چکیده

A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with high yield and high enantioselectivity.

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منابع مشابه

Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones.

A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with ...

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Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04609f Click here for additional data file.

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic a-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017