58131-63-8Relevant academic research and scientific papers
Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins
Page, Claire G.,Cooper, Simon J.,Dehovitz, Jacob S.,Oblinsky, Daniel G.,Biegasiewicz, Kyle F.,Antropow, Alyssa H.,Armbrust, Kurt W.,Ellis, J. Michael,Hamann, Lawrence G.,Horn, Evan J.,Oberg, Kevin M.,Scholes, Gregory D.,Hyster, Todd K.
supporting information, p. 97 - 102 (2021/01/12)
Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.
SYNTHESIS OF SELENOPSILOCINE (3-DIMETHYLAMINOETHYL-4-HYDROXYBENZOSELENOPHENE)
Dari, Abdelmjid,Christiaens, Leon E.,Renson, Marcel J.
, p. 1737 - 1748 (2007/10/02)
Starting from the known 6-methoxyanthranilic acid (5), we have synthesized in six steps the selenium analogue of psilocine (1c).The key intermediate is the 4-methoxyselenoindoxyl (8), which is condensed with the dimethylaminocarbamoylmethylenetriphenylpho
Synthesis and Structural Characterization of Gold-(I), -(III) and Silver(I) Complexes of the Ylide Ligand Ph3P=CHC(O)NMe2. Crystal Structure of >ClO4
Vicente, Jose,Chicote, Maria-Teresa,Lagunas, Maria-Cristina,Jones, Peter G.
, p. 2579 - 2584 (2007/10/02)
The reaction between (tht = tetrahydrothiophene) and the ylide Ph3P=CHC(O)NMe2 gives > 1, which reacts with chlorine to give > 2 and with the same ylide and NaClO4 to form 2>ClO4 3.The analogous silver complex 2>ClO4 4 is obtained by the reaction of AgClO4 with the ylide in molar ratio 1: 2.The phosphonium salt ClO4 reacts with (acac = acetylacetonate) to give (PPh3)>ClO4 5 or >ClO4 6 depending on the reaction conditions.The structure of 6 was confirmed by an X-ray diffraction study at -95 deg C , a = 11.572(3), b = 11.836(3), c = 21.627(7) Angstroem, α = 78.29(2), β = 87.19(2), γ = 75.65(2) deg, R = 0.076>; the Au...Au bond length is 2.938(1) Angstroem.
