118138-63-9Relevant academic research and scientific papers
Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
Azzena, Francesca,Calvani, Federico,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco,Pineschi, Mauro
, p. 10601 - 10626 (1995)
The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the regiochemical outcome of these systems is examined. In some cases, the use of LiClO4 or Mg(ClO4)2 as the promoting metal salt makes it possible the obtainment of a nice regioalternating process.
The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: The first endo-mode epoxide-opening reaction through an intramolecular metal chelate
Sasaki, Minoru,Tanino, Keiji,Hirai, Atsushi,Miyashita, Masaaki
, p. 1789 - 1791 (2007/10/03)
(Matrix presented) Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN 3-(CH3O)3B, NaSPh-(CH3O) 3B, or NaCN-(C2H5/
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.
