73500-58-0Relevant academic research and scientific papers
Asymmetric Michael addition of malonic diesters to acrylates by phase-transfer catalysis toward the construction of quaternary stereogenic α-carbons
Odanaka, Yuki,Kanemitsu, Takuya,Iwasaki, Kanako,Mochizuki, Yukiko,Miyazaki, Michiko,Nagata, Kazuhiro,Kato, Masaru,Itoh, Takashi
supporting information, p. 209 - 219 (2018/12/11)
A highly enantioselective construction of an all-carbon quaternary stereogenic center at the α-position of malonic diesters has been achieved by Michael addition using phase-transfer catalysis. The reaction of α-monosubstituted malonates with acrylates in
Chemoselective Transesterification of Acrylate Derivatives for Functionalized Monomer Synthesis Using a Hard Zinc Alkoxide Generation Strategy
Nakatake, Daiki,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 3696 - 3699 (2016/08/20)
A new practical method for the synthesis of functionalized acrylate derivatives with the view to prepare functional polymers was explored. Hard zinc alkoxide generation enabled the highly chemoselective transesterification of acrylate derivatives over the undesired conjugate addition, which caused polymerization. The combined use of the catalytic zinc cluster Zn4(OCOCF3)6O and 4-(dimethylamino)pyridine delivered various functionalized acrylate derivatives through the transesterification of commercially available methyl acrylate derivatives with functionalized alcohols under mild conditions.
A bifunctional β-isocupreidine derivative as catalyst for the enantioselective morita-baylis-hillman reaction and a mechanistic rationale for enantioselectivity
Martelli, Gianluca,Orena, Mario,Rinaldi, Samuele
experimental part, p. 4140 - 4152 (2012/09/08)
Starting from β-isocupreidine (β-ICD), a series of difunctional catalysts were synthesized to ascertain their usefulness in the asymmetric Morita-Baylis-Hillman (MBH) reaction. The trichloroacetylcarbamate derivative was found to give the (R)-MBH adducts in excellent optical purities (90-99% ee) and moderate to good yields (43-83%), in some cases, better than β-ICD. A number of acrylates were also tested and 2,6-dimethyl-4-nitrophenyl acrylate was identified as a suitable alternative to the popular hexafluoroisopropyl acrylate, with both the β-ICD and trichloroacetylcarbamate derivatives. The mechanism of the rate- and selectivity-determining step was ascertained by means of experimental observations and a computational investigation aimed at clarifying the transition state structures is reported. These studies have clarified the reasons for the effectiveness of these structurally related catalysts in the asymmetric MBH reaction between acrylates and aldehydes. β-Isocupreidine derivatives were used tocatalyze the asymmetric Morita-Baylis-Hillman (MBH) reaction, giving the (R)-MBH adducts in excellent optical purities and moderate to good yields. Both 2,6-dimethyl-4-nitrophenyl and hexafluoroisopropyl acrylate could be used. The rate- and selectivity-determining step was identified and the structures of the preferred transition states were computed.
Solvent-free transesterification in a ball-mill over alumina surface
Chatterjee, Tanmay,Saha, Debasree,Ranu, Brindaban C.
experimental part, p. 4142 - 4144 (2012/08/28)
An efficient procedure for transesterification has been developed in a ball-mill in the absence of any solvent, acid/base or metal catalyst. A variety of methyl, ethyl, allyl esters have been transesterified to higher benzyl and other esters in high yields by this procedure.
Observation of an acryloyl-thiamin diphosphate adduct in the first step of clavulanic acid biosynthesis
Merski, Matthew,Townsend, Craig A.
, p. 15750 - 15751 (2008/09/20)
The first committed biosynthetic step toward clavulanic acid, the clinically important β-lactamase inhibitor, is catalyzed by the thiamin diphosphate (ThDP)-dependent enzyme N2-(2-carboxyethyl)arginine synthase (CEAS). This protein carries out
