117340-83-7Relevant academic research and scientific papers
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.
Chemoenzymatic dynamic kinetic resolution of β-halo alcohols. An efficient route to chiral epoxides
Pamies, Oscar,Baeckvall, Jan-E.
, p. 9006 - 9010 (2007/10/03)
Enzymatic resolution of β-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when β-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.
