Enantioselective Vinylogous Addition of Enones to Allenes Enabled by Synergistic Borane/Palladium Catalysis DOI
Heng Luo, Ming Zhang,

Zequn Xing

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

Herein, we report a method for enantioselective vinylogous addition of enones to alkoxyallenes enabled by synergistic borane/palladium catalysis. The inductive effect provided borane coordination the ketone was essential closing gap between conditions needed generation dienolate and those initiation palladium catalytic cycle protonation metal catalyst. Furthermore, accomplished first example stereodivergent synthesis with chiral borane/transition-metal catalysts.

Language: Английский

Chemodivergent Tandem Hydroalkylation and Hydroalkenoxylation of Conjugated Enynes DOI

Bo-Yuan Xie,

Zhi‐Tao He

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(13), P. 9742 - 9751

Published: June 14, 2024

Due to the instability and weak O-nucleophilicity of enol, carbonyl compounds prefer function as C-nucleophiles instead O-nucleophiles in extensively studied transition metal-catalyzed hydrofunctionalizations unsaturated bonds. The corresponding hydroalkenoxylation reaction has thus long been unexplored. Here, we describe a chemodivergent protocol for challenging reactions. Dictated by Pd catalyst bearing different ligands, both 5-exo-trig 6-endo-trig processes are demonstrated be feasible between 1,3-enynes ketoesters, polysubstituted hydrofurans hydropyrans achieved good yields excellent chemoselectivities. In addition, enantioselective is also explored under an Rh moderate efficiency but with high stereoselectivities. Mechanistic studies corroborate designed tandem hydroalkylation uncover that ligand-to-ligand hydrogen transfer process might involved turnover-limiting step hydroalkenoxylation.

Language: Английский

Citations

5
Substrate NOBINAc ligand affinity for PdII-catalyzed enantioselective C–H activation over reactive β-C–H bonds in ferrocenyl amines DOI Creative Commons
Devendra Parganiha, Raviraj Ananda Thorat, Ashwini Dilip Dhumale

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

Ferrocenyl amines as directing groups for C–H activation have limitations they are prone to undergo oxidation, allylic deamination, and β-hydride elimination.

Language: Английский

Citations

1
Enantioselective Vinylogous Addition of Enones to Allenes Enabled by Synergistic Borane/Palladium Catalysis DOI
Heng Luo, Ming Zhang,

Zequn Xing

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

Herein, we report a method for enantioselective vinylogous addition of enones to alkoxyallenes enabled by synergistic borane/palladium catalysis. The inductive effect provided borane coordination the ketone was essential closing gap between conditions needed generation dienolate and those initiation palladium catalytic cycle protonation metal catalyst. Furthermore, accomplished first example stereodivergent synthesis with chiral borane/transition-metal catalysts.

Language: Английский

Citations

0