Citation: Ruilong Geng, Lingzi Peng, Chang Guo. Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis[J]. Chinese Chemical Letters, ;2024, 35(8): 109433. doi: 10.1016/j.cclet.2023.109433 shu

Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

plz@ustc.edu.cn

guochang@ustc.edu.cn

Received Date: 8 August 2023
Revised Date: 30 November 2023
Accepted Date: 11 December 2023
Available Online: 20 December 2023

Figures(5)

The dynamic kinetic asymmetric transformation of racemic propargylic ammonium salts with prochiral aldimine esters through a stereodivergent propargylation is catalyzed by dual nickel and copper catalysis. Thus, a diverse range of optically active α-quaternary amino esters were produced via CN bond cleavage with high reaction efficiency and stereoselectivity (up to > 99% ee). By selection of the appropriate pairwise combination of catalyst configurational isomers, all four possible stereoisomers of the corresponding propargylation products are obtained in high yields with excellent regio-, diastereo-, and enantioselectivities.
- Stereodivergent propargylation,
- Dual catalysis,
- C–N bond cleavage,
- Azaomethine ylides,
- Internal propargylic ammonium salts,
- Excellent stereoselectivity
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