76142-48-8Relevant academic research and scientific papers
Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines
Igarashi, Tomohito,Tayama, Eiji,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information, p. 6874 - 6877 (2019/04/10)
A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.
Stereoselective synthesis of Z-α-aryl-α,β-unsaturated esters
Mani, Neelakandha S.,Mapes, Christopher M.,Wu, Jiejun,Deng, Xiaohu,Jones, Todd K.
, p. 5039 - 5042 (2007/10/03)
An efficient method for the stereoselective synthesis of (Z)-α-arylacrylates is described. Treatment of α-hydroxyesters with triflic anhydride and pyridine at 0 °C followed by warming to room temperature afforded the corresponding (Z)-α-aryl-α,β- unsatura
Hydroxylation of carbanions with lithium teri-butyl peroxide acting as an oxenoid
Julia, Marc
, p. 15 - 24 (2007/10/03)
The lithium salt of terf-butyl hydroperoxide can convert alkyl, vinyl, aryl carbanions, acetylides and various enolates into the corresponding hydroxylated derivatives in good yields and under mild conditions. Eisevier.
HIGHLY ENANTIOSELECTIVE SYNTHESES OF α-HYDROXYACIDS USING N-BENZYL-4,4,7α-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE AS A CHIRAL ADJUVANT
He, Xu-Chang,Eliel, Ernest L.
, p. 4979 - 4988 (2007/10/02)
Addition of Grignard and organolithium reagents to as well as hydride reduction of 2α-benzoyl-N-benzyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (2, Y = C6H5CO) and addition of phenylmagnesium bromide to the corresponding 2-acetyl analog (11) proceed in highly diastereoselective fashion to produce virrtually exclusively the diastereomer predicted on the basis of Cram's chelate rule if chelation involves the ring oxygen atom.Mild acid hydrolysis of the adducts followed by selective oxidation produces highly enantiomerically pure α-hydroxyacids with clean recovery of the chiral adjuvant.
