Pd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers

Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chemistry. Herein, we report a facile and efficient protocol to construct vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo-...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-03, Vol.58 (21), p.3513-3516
Main Authors: Huang, Shuai, Zhang, Gao-Peng, Jiang, Yang-Jie, Yu, Fei-Le, Ding, Chang-Hua, Hou, Xue-Long
Format: Article
Language:English
Subjects:
Alkylation
Asymmetry
Carbon
Enantiomers
Hydrazones
Palladium
Reagents
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Summary:Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chemistry. Herein, we report a facile and efficient protocol to construct vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo- and enantioselectivities Pd-catalyzed umpolung asymmetric allylic alkylation of hydrazones with monosubstituted allyl reagents by using Kündig-type chiral N-heterocyclic carbene as the ligand. The control experiments revealed that the reaction proceeds the inner-sphere mechanism.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc07074f