title: Synthesis of enantiopure 1,2-azido and 1,2-amino alcoholsviaregio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.
abstract: 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 PPh3in water/THF, and then converted into the Boc or acetamide derivatives.
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Hai-Yang
authors: HY
authors: Wang
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Kun
authors: K
authors: Huang
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Melvin
authors: M
authors: De Jesús
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Sandraliz
authors: S
authors: Espinosa
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Luis E
authors: LE
authors: Piñero-Santiago
authors: Department of Chemistry, University of Missouri, Columbia, MO 65211, USA.
authors: Charles L
authors: CL
authors: Barnes
authors: Department of Chemistry, University of Puerto Rico-Humacao, CALL BOX 860, Humacao, PR 00792, USA.
authors: Margarita
authors: M
authors: Ortiz-Marciales