118043-40-6Relevant academic research and scientific papers
Regioselective Ring-opening Reactions of 2,3-Epoxy Alcohols with Sodium Azide Supported on Zeolite CaY
Onaka, Makoto,Sugita, Keisuke,Izumi, Yusuke
, p. 1327 - 1328 (1986)
Sodium azide supported on zeolite CaY induces C-3 ring-opening of 2,3-epoxy alcohols to afford 3-azido-1,2-diols in much higher regioselectivity than a conventional reagent system of NaN3-NH4Cl in MeOH-H2O.The cation in zeolite greatly influences the regi
Solid-Supported Sodium Azide Reagents: Their Preparation and Reactions with Epoxides
Onaka, Makoto,Sugita, Keisuke,Izumi, Yusuke
, p. 1116 - 1123 (2007/10/02)
Sodium azide is supported on three types of porous solid acids (zeolite, alumina, and silica gel) and applied to several reactions with epoxides.A systematic investigation reveals that the reactivities of the supported reagents are greatly influenced by loading amounts of NaN3, amounts of adsorbed water in the reagents, acidic properties of the solid acids, and reaction solvents.For demonstrating the utility of supported NaN3 reagents in selective organic syntheses, nucleophilic ring-opening reactions of 2,3-epoxy alcohols with the supported reagents are examined.Among the supported reagents, only the Ca2+-exchanged zeolite-supported reagent induces a C-3 ring opening in a highly regioselective manner (>90percent).It is deduced that the role of calcium ions in the zeolite is to increase the acid strength of the zeolite facilitating the ring cleavage of epoxides and to fix the conformation of epoxy alcohols through forming chelate complexes with calcium ions.
Regioselective Azide Opening of 2,3-Epoxy Alcohols by : Synthesis of α-Amino Acids
Caron, Maurice,Carlier, Paul R.,Sharpless, K. Barry
, p. 5185 - 5187 (2007/10/02)
Treatment of 2,3-epoxy alcohols with affords the corresponding 3-azido 1,2-diols, which are readily transformed in two steps to the α-amino acids.
A HIGHLY REGIO- AND STEREOSELECTIVE RING-OPENING OF 2,3-EPOXY ALCOHOLS WITH TRIMETHYLSILYL AZIDE-DIETHYLALUMINIUM FLUORIDE SYSTEM
Maruoka, Keiji,Sano, Hiromi,Yamamoto, Hisashi
, p. 599 - 602 (2007/10/02)
A new approach to the mild and selective synthesis of 3-azidodiols has been described which involves a highly regio- and stereoselective ring-opening of 2,3-epoxy alcohols with trimethylsilyl azide and diethylaluminium fluoride.
