97643-05-5Relevant academic research and scientific papers
Lithium naphthalenide induced reductive cleavage of α,β-epoxy ketones: An efficient procedure for the preparation of β-hydroxy ketones
Jankowska, Renata,Mhehe, George L.,Liu, Hsing-Jang
, p. 1581 - 1582 (2007/10/03)
Lithium naphthalenide presents itself as a mild and efficient reagent for the cleavage of α,β-epoxy ketones to give the corresponding β-hydroxy ketones in good yields.
The organoselenium-mediated reduction of α,β-epoxy ketones, α,β-epoxy esters, and their congeners to β-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues
Miyashita, Masaaki,Suzuki, Toshio,Hoshino, Masahide,Yoshikoshi, Akira
, p. 12469 - 12486 (2007/10/03)
Novel methods for the reduction of α,β-epoxy ketones, α,β-epoxy esters (glycidic esters), and their congeners to β-hydroxy carbonyl compounds (aldols) by the use of organoselenium reagents are described. The reagents, a sodium phenylseleno(triethyl)borate complex Na[PhSeB(OEt)3] easily prepared by reduction of (PhSe)2 with NaBH4 in EtOH and benzeneselenol (PhSeH) generated in situ from the borate complex by addition of acetic acid, have been demonstrated to serve as excellent reducing agents for these transformations. The organoselenium-mediated reduction of α,β-epoxy carbonyl compounds regiospecifically occurs at the α-carbon to produce a wide variety of cyclic (intramolecular) aldols as well as acyclic (intermolecular) ones in excellent yields. Quantitative mechanistic studies have revealed that the organoselenium-mediated reduction proceeds via an α-substitution process in contrast to the common electron transfer reducing agents.
ORGANOSELENIUM-MEDIATED REDUCTION OF α,β-EPOXY KETONES TO β-HYDROXY KETONES: A NEW ACCESS TO INTER- AND INTRAMOLECULAR ALDOLS
Miyashita, Masaaki,Suzuki, Toshio,Yoshikoshi, Akira
, p. 4293 - 4296 (2007/10/02)
The organoselenium-mediated reduction of α,β-epoxy ketones has been demonstrated to be a promising entry to a variety of cyclic and acyclic aldols.
Stereochemistry of the Reductive Alkylation of α,β-Epoxy Ketones
McChesney, James D.,Thompson, Thomas N.
, p. 3473 - 3481 (2007/10/02)
α-Epoxy ketones have been found to be useful intermediates for regiospecific alkylation of ketones.We have examined the steric course of the alkylation and shown it to be highly stereoselective.
CHEMO- AND REGIOSELECTIVE REDUCTION OF α,β-EPOXY KETONES TO β-HYDROXY KETONES BY SODIUM HYDROGENTELLURIDE
Osuka, Atsuhiro,Taka-Oka, Koji,Suzuki, Hitomi
, p. 271 - 272 (2007/10/02)
α,β-Epoxy ketones were chemo- and regioselectively reduced to β-hydroxy ketones by sodium hydrogentelluride in good yields.
