107076-91-5Relevant academic research and scientific papers
Cesium propionate as an epoxide cleavage and inversion reagent
Arbelo, David O,Prieto, José A
, p. 4111 - 4114 (2002)
A new epoxide inversion method, based on cesium propionate as the epoxide-cleaving agent, was developed. The initial epoxide-cleavage reaction produced a pair of regioisomeric propionates that were mesylated and methanolyzed to produce the inverted epoxide. Several new epoxides were prepared by this method, including 3,4-epoxy alcohols, which are important precursors for polypropionate synthesis.
Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes
Shing, Tony K. M.,Leung, Gulice Y. C.,Luk, To
, p. 7279 - 7289 (2007/10/03)
Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric effect, and electronic effect involving π-π interaction between phenyl groups of substrate and of catalyst did not appear to be operative in our system.
Useful base promoted elaborations of oxiranyl ethers
Thurner, Angelika,Faigl, Ferenc,Toke, László,Mordini, Alessandro,Valacchi, Michela,Reginato, Gianna,Czira, Gábor
, p. 8173 - 8180 (2007/10/03)
Functionalized oxiranyl ethers can be regio- and stereoselectively converted into hydroxy oxetanes or cis-diols by treatment with organometallic bases. These two rearrangements can be conveniently carried out either using different reaction conditions sta
Deracemization of anti-1,2-diols leading to trans-epoxides via oxazaborolidine-mediated enantiomer-differentiating ring-cleavage of acetal derivatives
Harada, Toshiro,Nakamura, Tomohito,Kinugasa, Motoharu,Oku, Akira
, p. 503 - 506 (2007/10/03)
An enantioconvergent transformation of racemic anti-1,2-diols to enantiomerically enriched (71-96% ee) trans-epoxides is realized via chiral oxazaborolidine-mediated enantiomer-differentiating ring-cleavage reaction of the acetal derivatives.
Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 5. Synthesis and Reactions of Some 2,3-Epoxy-1-alkanol Derivatives
Chini, Marco,Crotti, Paolo,Flippin, Lee A.,Gardelli, Christina,Giovani, Elena,et al.
, p. 1221 - 1227 (2007/10/02)
In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivati
Regioselective Opening of Epoxy Alcohols: Mild Chemo- and Stereoselective Preparation of Iodohydrins and 1,2-Diols
Bonini, Carlo,Righi, Giuliana,Sotgiu, Giovanni
, p. 6206 - 6209 (2007/10/02)
Several 2,3-epoxy alcohols have been opened, at -60 deg C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity.The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols.The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use.Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile.The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodiode ion.
