Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 9, P. 100069 - 100069
Published: Feb. 28, 2024
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(33)
Published: May 31, 2024
Catalytic enantioselective alkenylation of aldehydes with easily accessible alkenyl halides promoted by a chiral cobalt complex derived from newly developed tridentate bisoxazolinephosphine is presented. Such processes represent an unprecedented reaction pathway for catalysis and general approach that enable rapid construction highly diversified enantioenriched allylic alcohols containing 1,1-, 1,2-disubstituted trisubstituted alkene as well axial stereogenicity in up to 99 % yield : 1 er without the need preformation alkenyl-metal reagents. DFT calculations revealed origin enantioselectivity.
Language: Английский
Citations
9
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(37)
Published: June 25, 2024
Abstract Chiral allylic alcohols are highly prized in synthetic chemistry due to their versatile reactivity stemming from both alkenyl and hydroxyl functionalities. While the Nozaki–Hiyama–Kishi (NHK) reaction is a widely used method for synthesis of alcohols, it suffers drawbacks such as use toxic chromium salts, high amounts metal reductants, poor enantiocontrol. To address these limitations, we present novel approach involving metallaphotoredox‐catalyzed asymmetric NHK production chiral alcohols. This marries (pseudo)halides with aldehydes, leveraging synergistic blend nickel catalyst photocatalyst. innovative technique enables oxidative addition insertion just using nickel, diverging significantly conventional pathway mediated by salts. The adoption this methodology holds immense promise crafting spectrum intricate compounds, particularly those significance pharmaceuticals. Detailed experimental investigations have shed light on metallaphotoredox process, further enhancing our understanding enabling advancements.
Language: Английский
Citations
5
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: May 31, 2024
Abstract Catalytic enantioselective alkenylation of aldehydes with easily accessible alkenyl halides promoted by a chiral cobalt complex derived from newly developed tridentate bisoxazolinephosphine is presented. Such processes represent an unprecedented reaction pathway for catalysis and general approach that enable rapid construction highly diversified enantioenriched allylic alcohols containing 1,1‐, 1,2‐disubstituted trisubstituted alkene as well axial stereogenicity in up to 99 % yield : 1 er without the need preformation alkenyl–metal reagents. DFT calculations revealed origin enantioselectivity.
Language: Английский
Citations
0
Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(37)
Published: June 25, 2024
Abstract Chiral allylic alcohols are highly prized in synthetic chemistry due to their versatile reactivity stemming from both alkenyl and hydroxyl functionalities. While the Nozaki–Hiyama–Kishi (NHK) reaction is a widely used method for synthesis of alcohols, it suffers drawbacks such as use toxic chromium salts, high amounts metal reductants, poor enantiocontrol. To address these limitations, we present novel approach involving metallaphotoredox‐catalyzed asymmetric NHK production chiral alcohols. This marries (pseudo)halides with aldehydes, leveraging synergistic blend nickel catalyst photocatalyst. innovative technique enables oxidative addition insertion just using nickel, diverging significantly conventional pathway mediated by salts. The adoption this methodology holds immense promise crafting spectrum intricate compounds, particularly those significance pharmaceuticals. Detailed experimental investigations have shed light on metallaphotoredox process, further enhancing our understanding enabling advancements.
Language: Английский
Citations
0
Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)
Published: Sept. 4, 2024
Abstract Catalytic regio‐, diastereo‐ and enantioselective reductive coupling of 1,3‐dienes aldehydes through regio‐ oxidative cyclization followed by diastereoselective protonation promoted a chiral phosphine‐cobalt complex is presented. Such processes represent an unprecedented reaction pathway for cobalt catalysis that enable selective transformation the more substituted alkene in 1,3‐dienes, affording broad scope bishomoallylic alcohols without need pre‐formation stoichiometric amounts sensitive organometallic reagents up to 98 % yield, >98 : 2 regioselectivity, dr er. Application this method construction axial stereogenicity deuterated stereogenic center provided wide range multifunctional building blocks are otherwise difficult access. DFT calculations revealed origin stereoselectivity as well unique mechanism catalysis.
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)
Published: Sept. 4, 2024
Catalytic regio-, diastereo- and enantioselective reductive coupling of 1,3-dienes aldehydes through regio- oxidative cyclization followed by diastereoselective protonation promoted a chiral phosphine-cobalt complex is presented. Such processes represent an unprecedented reaction pathway for cobalt catalysis that enable selective transformation the more substituted alkene in 1,3-dienes, affording broad scope bishomoallylic alcohols without need pre-formation stoichiometric amounts sensitive organometallic reagents up to 98 % yield, >98 : 2 regioselectivity, dr er. Application this method construction axial stereogenicity deuterated stereogenic center provided wide range multifunctional building blocks are otherwise difficult access. DFT calculations revealed origin stereoselectivity as well unique mechanism catalysis.
Language: Английский
Citations
0
Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 9, P. 100069 - 100069
Published: Feb. 28, 2024
Language: Английский
Citations
0