113471-32-2Relevant articles and documents
Preparation of Optically Active 2-Furylcarbinols by Kinetic Resolution Using the Sharpless Reagent
Kobayashi,Yuichi,Kusakabe, Masato,Kitano, Yasunori,Sato, Fumie
, p. 1586 - 1587 (1988)
Enantioselective oxidation using TBHP and an asymmetric titanium-tartrate complex provides direct access to a variety of optically active 2-furylcarbinols.
Highly Enantioselective Hydrogenation of Enol Acetates Catalyzed by Ru-TunaPhos Complexes
Wu, Shulin,Wang, Weimin,Tang, Wenjun,Lin, Min,Zhang, Xumu
, p. 4495 - 4497 (2002)
(Matrix Presented) The chiral disphosphines with tunable dihedral angles (TunaPhos) have been used for asymmetric hydrogenation of enol acetates and dihedral-angle-dependent enantioselectivities were observed. C2-TunaPhos has been proved to be effective for Ru-catalyzed asymmetric hydrogenation of electron-deficient and other enol acetates.
Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation–Racemization and Enzymatic Resolution Cascade
El-Sepelgy, Osama,Brzozowska, Aleksandra,Rueping, Magnus
, p. 1664 - 1668 (2017/04/27)
A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation–dehydrogenation–hydrogenation of prochiral ketones. By merging the iron-catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones, as well as diketones, were reductively acylated. The corresponding products were isolated with high yields and enantioselectivities. The use of an iron catalyst together with molecular hydrogen as the hydrogen donor and readily available ethyl acetate as acyl donor make this cascade process highly interesting in terms of both economic value and environmental credentials.
Tuning lipase-catalysed kinetic resolution of 2-substituted thiophenes and furans: A scalable chemoenzymatic route to masked γ-bis-oxo-alcohols
Ferreira, Dartagnan S.P.,Ferreira, Jeiely G.,Filho, Everaldo F.S.,Princival, Jefferson L.
, p. 37 - 45 (2016/02/18)
The demand for greener and applicable approaches aiming at the synthesis of optically active compounds as single enantiomers has seen a significant growth worldwide. Since most of the chemically synthesized compounds are produced as racemates their kinetic resolution has been of great interest. For this purpose a number of chemo-enzymatic approaches were proposed. One of such approaches, the use of isolated lipases, is a well-established alternative. Herein we report the kinetic resolutions of 2-Substituted five-membered heteroaromatic rings. By optimizing the reaction conditions it was possible to produce (2-hydroxy)-2-substituted furans and thiophenes in high enantiomeric ratio (E > 200). Thus, racemic mixtures of compounds with slight structural differences were resolved. The current chemo-enzymatic strategy has been applied to a scalable approach leading to the formation of the enantiopure (S)-2i a well-known building block used for the synthesis of bioactive natural compounds.
