206276-07-5Relevant academic research and scientific papers
Asymmetric epoxidation of α,β-unsaturated ketones with hydrogen peroxide catalyzed by axially chiral guanidine base
Terada, Masahiro,Nakano, Megumi
experimental part, p. 1049 - 1055 (2009/06/28)
The enantioselective epoxidation of α,β-unsaturated ketones with hydrogen peroxide was demonstrated using axially chiral guanidine as a base catalyst. Hydrogen peroxide can be utilized as a cost-effective and atom-efficient oxidant in the present catalyti
Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt
Corey,Zhang, Fu-Yao
, p. 1287 - 1290 (2008/02/09)
(Matrix presented) Highly enantioselective (up to 130:1) epoxidation of a variety of α,β-enones to form α,β-epoxy ketones is described along with a rational analysis of the mechanistic basis for this strong absolute stereochemical control by the chiral ca
Phase-transfer-catalyzed asymmetric Darzens reaction
Arai, Shigeru,Shirai, Yoshiki,Ishida, Toshimasa,Shioiri, Takayuki
, p. 6375 - 6386 (2007/10/03)
Catalytic asymmetric Darzens reaction promoted by a chiral phase- transfer catalyst derived from cinchonine is described. The desired α,β- epoxy ketones were obtained by use of α-chloro acyclic and cyclic ketones as substrates with moderate to high enantiomeric excesses under mild reaction conditions. This methodology can be quite an effective protocol for practical asymmetric synthesis.
Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions
Arai, Shigeru,Shioiri, Takayuki
, p. 2145 - 2148 (2007/10/03)
The catalytic asymmetric Darzens condensation promoted by the quaternary ammonium salt (PTC A) derived from cinchonine as a phase-transfer catalyst is described. Treatment of phenacyl chloride with various aldehydes under mild reaction afforded he corresponding desired in good yield with good to moderate enantiomeric excess.
Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain
Adger, Brian M.,Barkley, James V.,Bergeron, Sophie,Cappi, Michael W.,Flowerdew, Benjamin E.,Jackson, Mark P.,McCague, Ray,Nugent, Thomas C.,Roberts, Stanley M.
, p. 3501 - 3507 (2007/10/03)
Poly-L-leucine catalyses the asymmetric epoxidation of enones 1-6 efficiently in a non-aqueous medium to provide the epoxy ketones 7-12 (70-91% yield; 80 to ≥95% ee). The strategy was used to make diltiazem 16 and the Taxol side chain 23 in single enantiomer form.
