156848-00-9Relevant academic research and scientific papers
A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester
Han, Guoxia,Hruby, Victor J.
, p. 4281 - 4283 (2001)
Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.
Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone
Stockton, Kieran P.,Greatrex, Ben W.
, p. 7520 - 7528 (2016/08/16)
The biorenewable chiral synthon (-)-levoglucosenone has been converted to enantiopure cyclopropyl esters using the base-promoted carbocyclisation of 4,5-epoxyvalerates. This protocol was applied to the enantiospecific synthesis of the GABAc receptor agonist (1R,2R)-trans-2-aminomethylcyclopropanecarboxylic acid ((-)-TAMP) and its enantiomer. The process was also extended to generate 1,1,2- and 1,2,3-trisubstituted cyclopropanes resulting in a formal synthesis of the selective glutamate receptor antagonist PCCG-4.
Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral γ-Butyrolactones
Stockton, Kieran P.,Merritt, Christopher J.,Sumby, Christopher J.,Greatrex, Ben W.
, p. 6999 - 7008 (2015/11/16)
The chiral pool material (-)-levoglucosenone (6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, LGO) has been substituted by using a series of Pd-mediated cross-coupling reactions. Iodination of LGO followed by Suzuki-Miyaura cross-coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)2 afforded 3-aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2-position was achieved with aryl iodides with K3PO4 as base and SPhos ligand with Pd(OAc)2 (1-5 mol-%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd(OAc)2, and P(o-tol)3. The products were converted, either directly or after alkene reduction, through a Baeyer-Villiger oxidation into chiral 3- and 4-substituted 5-(hydroxymethyl)dihydrofuran-2(3H)-ones. Three new cross-coupling approaches to the derivatization of levoglucosenone are described and the products converted into butyrolactones.
1,2-stereochemical induction in the PdII-catalyzed conjugate addition of boronic acids
Roscales, Silvia,Sánchez, Francisco,Csák?, Aurelio G.
, p. 1754 - 1763 (2015/05/27)
Palladium(II) catalysis has been used in the substrate-controlled 1,2-chiral induction of the conjugate addition of boronic acids to enantiopure α,β-unsaturated ketones and esters without competition from the Mirozoki-Heck reaction. Bedford's palladacycle
Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to γ-alkoxy-α,β-enoates
Kireev, Artem S.,Manpadi, Madhuri,Kornienko, Alexander
, p. 2630 - 2640 (2007/10/03)
Current models used to predict the stereochemical outcome of organocopper conjugate addition processes focus on the nucleophilic addition step as stereochemistry-determining. Recent kinetic, NMR, kinetic isotope effect, and theoretical density functional
Highly anti-selective conjugate addition of arylcuprates to a γ-alkoxy-α,β-enoate. A new method to address stereochemical challenges presented by Amaryllidaceae alkaloids
Manpadi, Madhuri,Kornienko, Alexander
, p. 4433 - 4437 (2007/10/03)
Various substituted arylcuprates undergo stereocontrolled additions to a d-mannitol-derived γ-alkoxy-α,β-enoate with exclusive anti-selectivity. The method is well suited for the preparation of a broad range of biologically active Amaryllidaceae alkaloids
Synthesis of some 2-C-alkyl-2,3-dideoxy-α,β-L-glycero-tetrurono-1,4-lactones. Evaluation as antitumor agents
Blazis, Vincent J.,Hawkins, Elma S.,Baker, David C.
, p. 225 - 234 (2007/10/02)
A series of 3-C-alkyl-2,3-dideoxy-5-O-trityl-D-erythro-pentono-1,4-lactones were detritylated.The resultant free-hydroxy compounds were converted to their respective 2-C-alkyl-2,3-dideoxy-α,β-L-glycero-tetrurono-1,4-lactones (L-sugar numbering) in a one-v
