19922-82-8Relevant articles and documents
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Williams et al.
, p. 993,994-996 (1975)
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Tandem transfer hydrogenation-epoxidation of ketone substrates catalysed by alkene-tethered Ru(ii)-NHC complexes
Malan, Frederick P.,Singleton, Eric,Van Rooyen, Petrus H.,Landman, Marilé
supporting information, p. 8472 - 8481 (2019/06/14)
A series of nine cyclopentadienyl Ru(ii)-NHC complexes (1-9) have been synthesised by systematically varying the ligand and/or ligand substituents: η5-C5H4R′ (R′ = H, Me), EPh3 (E = P, As), NHC (Im, BIm), where NHC = Im(R)(R′) (R, R′ = Me, Bn, 4-NO2Bn, C2H4Ph, C4H7). Each of the Ru(ii)-NHC complexes features an N-alkenyl tether to attain bidentate NHC ligands. All complexes found application as catalysts in the tandem transfer hydrogenation and epoxidation reactions of carbonyl substrates. The catalytic activity of the complexes was shown to be similar, with efficiencies of up to 69% conversion after 18 hours and varying alcohol:epoxide selectivity for a variety of electronically diverse carbonyl substrates. Complex 3, with a nitro-containing substituent on the NHC ligand, was the only complex that showed preference for the alcohol product over the epoxide after 18 hours of reaction time.
Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH
Mikleu?evi?, Ana,Primo?i?, Ines,Hrenar, Tomica,Salopek-Sondi, Branka,Tang, Lixia,Elenkov, Maja Majeri?
, p. 930 - 935 (2016/09/13)
Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.