50468-22-9Relevant articles and documents
Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system
Zhang, Jian-Dong,Yang, Xiao-Xiao,Jia, Qiao,Zhao, Jian-Wei,Gao, Li-Li,Gao, When-Chao,Chang, Hong-Hong,Wei, Wen-Long,Xu, Jian-He
, p. 70 - 74 (2019/01/10)
A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97-99% ee and 79-99% conversion from readily available racemic epoxides.
Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation
Kim, Juryoung,De Castro, Kathlia A.,Lim, Minkyung,Rhee, Hakjune
supporting information; experimental part, p. 3995 - 4001 (2010/07/05)
Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced α, β, γ, and δ-keto esters having α-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols.
Product distributions from the OH radical-induced oxidation of but-1-ene, methyl-substituted but-1-enes and isoprene in NO(x)-free air
Benkelberg,Boge,Seuwen,Warneck
, p. 4029 - 4039 (2007/10/03)
Product distributions resulting from the OH-induced oxidation of but-1-ene, 2-methylbut-1-ene, 3-methylbut-1-ene and isoprene in air were measured in the absence of nitrogen oxides and compared with predictions based on currently accepted oxidation mechanisms. In the case of butenes, the observed distributions of carbonyl compounds, hydroxyketones, hydroxyalkanals and diols were evaluated to obtain probabilities for the initial attack of OH radical on the outer position of the double bond (y = 0.90 ± 0.03 for 2-Me-but-1-ene and y = 0.76 ± 0.05 for both but-1-ene and 3-Me-but-1-ene), for the probability of formation of stable products in the self-reaction of secondary β-hydroxyperoxyl radicals (k(ssb)/k(ss) = 0.29 ± 0.07 for but-1-ene and k(ssb)/k(ss) = 0.19 ± 0.06 for 3-Me-but-1-ene), and for the ratio of the reaction with oxygen vs. decomposition of β-hydroxyalkoxyl radicals, k3[O2]/(k4 + k3[O2]) = 0.25 ± 0.04 for but-1-ene and = 0.38 ± 0.04 for 3-Me-but-1-ene. The last two values disagree with other published data, which suggest a smaller effect of oxygen. The oxidation of isoprene produced methacrolein and methyl vinyl ketone with a ratio 0.93 ± 0.10, the ratio of methyl vinyl ketone and 3-methylfuran was 7.3 ± 1.0. Other products were 1-hydroxy-3-methylbut-3-en-2-one (identified by mass spectrometry) and 3-methyl-3-oxo-butane (tentatively identified). The overall product distribution was complex and could not be fully elucidated. Computer simulations based on several mechanisms applied the relative probabilities for OH addition found for the but-1-enes. Comparison with the experimental data suggests probabilities for OH addition to the methylated double bond of 0.504 ± 0.027 (outer position) and 0.056 ± 0.003 (inner position), and to the non-methylated double bond of 0.335 ± 0.023 (outer position) and 0.105 ± 0.008 (inner position).
