397869-61-3Relevant academic research and scientific papers
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.
Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water
Wang, Hai-Yang,Huang, Kun,De Jesús, Melvin,Espinosa, Sandraliz,Pi?ero-Santiago, Luis E.,Barnes, Charles L.,Ortiz-Marciales, Margarita
, p. 91 - 100 (2016/02/09)
A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (S)-epoxides by N3- in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl-2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives.
Coupling biocatalysis and click chemistry: One-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols
Cuetos, Aníbal,Bisogno, Fabricio R.,Lavandera, Iván,Gotor, Vicente
supporting information, p. 2625 - 2627 (2013/04/23)
A fully convergent one-pot two-step synthesis of different chiral 1,2,3-triazole-derived diols in high yields and excellent enantio- and diastereoselectivities has been achieved under very mild conditions in aqueous medium by combining a single alcohol dehydrogenase (ADH) with a Cu-catalysed 'click' reaction. The Royal Society of Chemistry 2013.
Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles
Rocha, Lenilson C.,Rosset, Isac G.,Melgar, Gliseida Z.,Raminelli, Cristiano,Porto, Andre? L. M.,Jeller, Alex H.
, p. 1427 - 1432 (2013/09/24)
As resoluc?o?es cine?ticas de (±)-β- azidofeniletano?is foram realizadas usando a lipase de Candida antarctica fornecendo os compostos enantiomericamente enriquecidos, (R)-β- azidofeniletano?is e acetato de (S)-β-azidofeniletila em bons excessos enantiome
Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing β-blocker analogues employing click chemistry
Ankati, Haribabu,Yang, Yan,Zhu, Dunming,Biehl, Edward R.,Hua, Ling
, p. 6433 - 6436 (2008/12/22)
(Chemical Equation Presented) Both antipodes of 2-azido-1-arylethanols were synthesized with excellent optical purity via enzymatic reduction of the corresponding α-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida m
