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

ABSTRACT: 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.

SUBMITTER: Zuo XD 

PROVIDER: S-EPMC5628337 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Bioinspired enantioselective synthesis of crinine-type alkaloids <i>via</i> iridium-catalyzed asymmetric hydrogenation of enones.

Zuo Xiao-Dong XD   Guo Shu-Min SM   Yang Rui R   Xie Jian-Hua JH   Zhou Qi-Lin QL  

Chemical science 20170703 9

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. ...[more]

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