Journal
CHEMICAL SCIENCE
Volume 13, Issue 38, Pages 11405-11410Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc04350e
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Funding
- NSFC [22171127, 21971101]
- Guangdong Basic and Applied Basic Research Foundation [2022A1515011806]
- Department of Education of Guangdong Province [2021KTSCX106, 2022JGXM054]
- Stable Support Plan Program of Shenzhen Natural Science Fund [20200925152608001]
- Thousand Talents Program for Young Scholars
- Pearl River Talent Recruitment Program [2019QN01Y261]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
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This study presents a straightforward protocol to build allylic dialkylated stereogenic centers by nickel-catalyzed regio- and enantioselective hydrovinylation. The reaction allows for the efficient construction of dialkylated allylic species in good yields with excellent enantioselectivities. It works for various alkenes and under mild conditions.
Tertiary dialkylated allylic stereogenic centers are widespread substructures in bioactive molecules and natural products. However, enantioselective access to dialkyl substituted allylic motifs remains a long-term challenge. Herein, a straightforward protocol to build allylic dialkylated stereogenic centers enabled by nickel-catalysed regio- and enantioselective hydrovinylation of isolated unactivated alkenes facilitated by a weakly coordinating group with vinyl bromides was developed, affording dialkylated allylic species in good yields with excellent enantioselectivities. The reaction distinguishes distinct alkenes and works for both terminal and internal aliphatic alkenes. The reaction proceeds under mild conditions and tolerates a wide range of functional groups.
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