124718-93-0Relevant articles and documents
Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade
Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk
, p. 5077 - 5085 (2021)
Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.
Preparation of Vicinal Azidohydrins by Reaction of Oxiranes with Triethylaluminium/Hydrogen Azide
Mereyala, Hari Babu,Frei, Bruno
, p. 415 - 418 (1986)
A novel, mild, and highly stereoselective transformation of epoxides to azidohydrins by treatment with Et3Al/HN3 in toluene is described.As an example for the versatility of the reaction, a polyfunctional compound, 14,15-epoxy-14,15-dihydromilbemycin D (1), was transformed to 14-azido-14,15-dihydro-15-hydroxymilbemycin D (2) in 61 percent yield.
Regioselective azidolysis of epoxides catalyzed with Ce(IV)
Iranpoor, Nasser,Kazemi, Foad
, p. 561 - 566 (1999)
Regioselective conversion of epoxides to 1,2-azidoalcohols was performed efficiently with sodium azide in t-butanol and in the presence of catalytic amounts of Ce(IV) as ceric ammonium nitrate (CAN).
Efficient one-pot click synthesis of β-hydroxy-1,2,3-triazoles catalyzed by copper(i)@phosphorated SiO2via multicomponent reaction in aqueous media
Naeimi, Hossein,Nejadshafiee, Vajihe
, p. 5429 - 5435 (2014)
Copper(i)-modified SiO2, in particular Cu(i)@phosphorated SiO2 (CPSi) has been found to effectively catalyze the multi-component synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. This novel heter
Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from: Ilumatobacter coccineus: A biocatalytic approach to 2-azido-2-aryl-1-ols
An, Miao,Liu, Wanyi,Zhou, Xiaoying,Ma, Ran,Wang, Huihui,Cui, Baodong,Han, Wenyong,Wan, Nanwei,Chen, Yongzheng
, p. 16418 - 16422 (2019/06/17)
Halohydrin dehalogenases are usually recognized as strict β-position regioselective enzymes in the nucleophile-mediated ring-opening of epoxides. Here we found the HheG from Ilumatobacter coccineus exhibited excellent α-position regioselectivity in the az
CuO supported 1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium chloride (MTMSP-Im/Cl) nanoparticles as an efficient simple heterogeneous catalysts for synthesis of β-azido alcohols
Fadavipoor,Badri,Kiasat,Sanaeishoar
, p. 1451 - 1458 (2019/06/13)
In the present study, CuO supported 1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium chloride (MTMSP-Im/Cl) is synthesized as a novel, efficient and eco-friendly heterogeneous nanocatalyst. This nanocatalyst was applied for selective ring opening of ep
Iron-Catalysed Remote C(sp3)?H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols
Torres-Ochoa, Rubén O.,Leclair, Alexandre,Wang, Qian,Zhu, Jieping
supporting information, p. 9477 - 9484 (2019/05/21)
In the presence of a catalytic amount of iron(III) acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ-azido ketones in good to excellent yields. This unprecedented distal γ-C(sp3)?H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5-hydrogen atom transfer (1,5-HAT) and iron-mediated redox azido transfer to the translocated carbon radical. TMSN3 served not only as a nitrogen source to functionalise the unactivated C(sp3)?H bond, but also as a reductant to generate the catalytically active FeII species in situ. Based on the same principle, a novel β-C(sp3)?H functionalisation of alcohols via N-acyloxy imidates was subsequently realised, leading, after hydrolysis of the resulting ester, to β-azido alcohols, which are important building blocks in organic and medicinal chemistry.
Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine
Ch Ghosh, Keshab,Banerjee, Isita,Sinha, Surajit
supporting information, p. 2923 - 2934 (2018/12/04)
A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.
Synthesis and characterization of supramolecule grafted on modified magnetic nanoparticles: new hybrid organic–inorganic phase transfer catalyst
Mouradzadegun, Arash,Boroon, Sadjad,Fard, Pegah Kazemian
, p. 367 - 374 (2017/02/10)
Abstract: In this study, for the first time, calix[4]resorcinarene was grafted on the silica-coated magnetic nanoparticles (MNPs-Si) which efficiently catalyze one-pot epoxide ring opening reaction in excellent yields in a very short reaction time. Variou
Acetic acid functionalized ionic liquid systems: An efficient and recyclable catalyst for the regioselective ring opening of epoxides with NaN3
Rezayati, Sobhan,Salehi, Elaheh,Hajinasiri, Rahimeh,Afshari Sharif Abad, Saeid
, p. 554 - 558 (2017/05/19)
In the present study, an environmentally benign, efficient, and solvent-free procedure was developed for the synthesis of 1,2-azidoalcohols by the regioselective ring opening of some epoxides with sodium azide (NaN3) in the presence of an aceti
