91230-07-8Relevant articles and documents
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.
Relay catalysis by a metal-complex/bronsted acid binary system in a tandem isomerization/carbon-carbon bond forming sequence
Sorimachi, Keiichi,Terada, Masahiro
supporting information; experimental part, p. 14452 - 14453 (2009/02/08)
A one-pot tandem isomerization/carbon-carbon bond forming sequence catalyzed by a ruthenium complex/Bronsted acid binary system is demonstrated. The method enables the use of readily available allylamides to deliver reactive imines under relay catalysis using a binary catalytic system. Subsequent Bronsted acid catalyzed carbon-carbon bond forming reactions of the generated imines with nucleophilic components afforded Friedel-Crafts and Mannich products in good yields. Copyright
Direct Conversion of Allylic Selenides to Protected Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Hopkins, Paul B.
, p. 3647 - 3650 (2007/10/02)
-