» Articles » PMID: 31082224

Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides

Overview
Journal J Am Chem Soc
Specialty Chemistry
Date 2019 May 15
PMID 31082224
Citations 8
Authors
Affiliations
Soon will be listed here.
Abstract

A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen-bearing fully substituted carbon centers.

Citing Articles

From Ground-State to Excited-State Activation Modes: Flavin-Dependent "Ene"-Reductases Catalyzed Non-natural Radical Reactions.

Fu H, Hyster T Acc Chem Res. 2024; 57(9):1446-1457.

PMID: 38603772 PMC: 11618812. DOI: 10.1021/acs.accounts.4c00129.


Metal-Catalyzed Enantioconvergent Transformations.

Yus M, Najera C, Foubelo F, Sansano J Chem Rev. 2023; 123(20):11817-11893.

PMID: 37793021 PMC: 10603790. DOI: 10.1021/acs.chemrev.3c00059.


Photoredox-Nickel Dual-Catalyzed -Alkylation of Secondary Nitroalkanes: Access to Sterically Hindered α-Tertiary Amines.

Rezazadeh S, Martin M, Kim R, Yap G, Rosenthal J, Watson D J Am Chem Soc. 2023; 145(8):4707-4715.

PMID: 36795911 PMC: 9992296. DOI: 10.1021/jacs.2c13174.


Asymmetric -Alkylation of Nitroalkanes Enzymatic Photoredox Catalysis.

Fu H, Qiao T, Carceller J, MacMillan S, Hyster T J Am Chem Soc. 2023; 145(2):787-793.

PMID: 36608280 PMC: 10859870. DOI: 10.1021/jacs.2c12197.


Fluorine in metal-catalyzed asymmetric transformations: the lightest halogen causing a massive effect.

Lauzon S, Ollevier T Chem Sci. 2022; 13(37):10985-11008.

PMID: 36320478 PMC: 9516955. DOI: 10.1039/d2sc01096h.


References
1.
Jones G, Martin J, McFarland C, Allen O, Hall R, Haley A . Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl-alkyl cross-coupling catalyst. J Am Chem Soc. 2006; 128(40):13175-83. DOI: 10.1021/ja063334i. View

2.
Ooi T, Takada S, Doda K, Maruoka K . Highly diastereo- and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes by chiral ammonium bifluoride catalysis. Angew Chem Int Ed Engl. 2006; 45(45):7606-8. DOI: 10.1002/anie.200602787. View

3.
Wilson J, Casarez A, MacMillan D . Enantioselective aldehyde alpha-nitroalkylation via oxidative organocatalysis. J Am Chem Soc. 2009; 131(32):11332-4. PMC: 3259685. DOI: 10.1021/ja904504j. View

4.
Lundin P, Fu G . Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides. J Am Chem Soc. 2010; 132(32):11027-9. PMC: 2924160. DOI: 10.1021/ja105148g. View

5.
Dobish M, Johnston J . Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles. Org Lett. 2010; 12(24):5744-7. PMC: 3005818. DOI: 10.1021/ol1025712. View