期刊
CHEMICAL SCIENCE
卷 12, 期 19, 页码 6712-6718出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc01115d
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资金
- 1000-Youth Talents Plan start up fund
- National Natural Science Foundation of China [21772183, 22071230]
- Fundamental Research Funds for the Central Universities [WK2060190086]
- University of Science and Technology of China
The nickel-catalyzed asymmetric reductive aryl-allylation reaction described in this study shows high stereo-selectivity in the synthesis of chiral compounds containing homoallyl substitution.
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.
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