62413-47-2Relevant articles and documents
Regio- and stereoselective reduction of trans-4-phenylbut-3-en-2-one using carrot, celeriac, and beetroot enzyme systems in an organic solvent
Majewska, Ewa,Koz?owska, Mariola
, p. 6331 - 6332 (2013)
(S)-trans-4-Phenylbut-3-en-2-ol has been obtained in excellent yields and with high enantiomeric excess in the reduction of trans-4-phenylbut-3-en-2-one using the comminuted roots of carrot (Daucus carota L.), celeriac (Apium graveolens L. var. rapaceum),
Self-Assembling All-Enzyme Hydrogels for Flow Biocatalysis
Peschke, Theo,Bitterwolf, Patrick,Gallus, Sabrina,Hu, Yong,Oelschlaeger, Claude,Willenbacher, Norbert,Rabe, Kersten S.,Niemeyer, Christof M.
, p. 17028 - 17032 (2018)
Continuous flow biocatalysis is an emerging field of industrial biotechnology that uses enzymes immobilized in flow channels for the production of value-added chemicals. We describe the construction of self-assembling all-enzyme hydrogels that are compris
Dramatic titanium alkoxide effect in the catalytic enantioselective addition of dialkylzincs to aldehydes
Nowotny, Stefan,Vettel, Stephan,Knochel, Paul
, p. 4539 - 4540 (1994)
The use of Ti(Ot-Bu)4, or related bulky titanium (IV) alkoxides, as cocatalysts instead of Ti(Oi-Pr)4 in the enantioselective addition of dimethylzinc to aldehydes in the prescence of the catalyst 2 (8 mol%) leads to a dramatic impro
Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes
Tran, Hai N.,Stanley, Levi M.
supporting information, p. 395 - 399 (2021/12/27)
The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.
Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones
Titze, Marvin,Heitk?mper, Juliane,Junge, Thorsten,K?stner, Johannes,Peters, René
supporting information, p. 5544 - 5553 (2021/02/05)
Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.