65702-08-1Relevant articles and documents
Chemoenzymatic Asymmetric Synthesis of Pyridine-Based α-Fluorinated Secondary Alcohols
Broese, Timo,Ehlers, Peter,Langer, Peter,von Langermann, Jan
, p. 3314 - 3318 (2021/10/12)
Fluoro-substituted and heteroaromatic compounds are valuable intermediates for a variety of applications in pharma- and agrochemistry and synthetic chemistry. This study investigates the chemoenzymatic preparation of chiral alcohols bearing a heteroaromatic ring with an increasing degree of fluorination in α-position. Starting from readily available picoline derivatives prochiral α-halogenated acyl moieties were introduced with excellent selectivity and 64–95 % yield. The formed carbonyl group was subsequently reduced to the corresponding alcohols using the alcohol dehydrogenase from Lactobacillus kefir, yielding an enantiomeric excess of 95–>99 % and up to 98 % yield.
Zheda-phos for general α-monoarylation of acetone with aryl chlorides
Li, Pengbin,Lue, Bo,Fu, Chunling,Ma, Shengming
supporting information, p. 1255 - 1259 (2013/06/27)
A new, readily available, and air-stable monophosphine ligand, i.e., Zheda-Phos, has been developed for the general and highly effective palladium-catalyzed monoarylation of acetone with aryl chlorides. The reaction rate is of first-order dependence with the aryl chloride. Copyright
The Wolff-Kishner Reduction of 2-Acetonyl Pyrazines and Pyridines. A Novel Rearrangement
Paine III, John B.
, p. 1463 - 1465 (2007/10/02)
Wolff-Kishner reduction of 1-(6-methylpyrazin-2-yl)-2-propanone leads to the formation of 2-isopropyl-6-methylpyrazine (2a), in addition to the expected 6-methyl-2-n-propylpyrazine.The by-product 2a is suggested to arise via a spirocyclopropylidene aza-anion, which serves as a conduit between the initial less-stable secondary 1-(2-pyrazinyl)-2-propyl carbanion and the more stable primary 2-(2-pyrazinyl)-1-propyl carbanion.Similar results were observed for the 1-(3-methylpyrazin-2-yl) and 1-(6-methylpyridin-2-yl)-2-propanones.The extent of by-product formation diminished in the pyridine ring system.Electrophilic activation of the ring appears essential since the benzene ring analog phenylacetone gave no detectable cumene under identical reaction conditions.