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Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

ABSTRACT: Herein we report a nickel-catalyzed asymmetric reductive aryl-allylation of aryl iodide-tethered unactivated alkenes, wherein both acyclic allyl carbonates and cyclic vinyl ethylene carbonates can serve as the coupling partners. Furthermore, the direct use of allylic alcohols as the electrophilic allyl source in this reaction is also viable in the presence of BOC anhydride. Remarkably, this reaction proceeds with high linear/branched-, E/Z- and enantio-selectivity, allowing the synthesis of various chiral indanes and dihydrobenzofurans (50 examples) containing a homoallyl-substituted quaternary stereocenter with high optical purity (90-98% ee). In this reductive reaction, the use of pregenerated organometallics can be circumvented, giving this process good functionality tolerance and high step-economy.

SUBMITTER: Lin Z

PROVIDER: S-EPMC8133004 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

Lin Zhiyang Z Jin Youxiang Y Hu Weitao W Wang Chuan C

Chemical science 20210409 19

Herein we report a nickel-catalyzed asymmetric reductive aryl-allylation of aryl iodide-tethered unactivated alkenes, wherein both acyclic allyl carbonates and cyclic vinyl ethylene carbonates can serve as the coupling partners. Furthermore, the direct use of allylic alcohols as the electrophilic allyl source in this reaction is also viable in the presence of BOC anhydride. Remarkably, this reaction proceeds with high linear/branched-, <i>E</i>/<i>Z</i>- and enantio-selectivity, allowing the syn ...[more]

PMID: 34040746

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