160422-56-0Relevant academic research and scientific papers
C2-Symmetric 1,2-Diamine/Copper(II) Trifluoromethanesulfonate Complexes as Chiral Ctalysts. Asymmetric Cyclopropanations of Styrene with Diazo Esters
Kanemasa, Shuji,Hamura, Satoshi,Harada, Etsuko,Yamamoto, Hidetoshi
, p. 7985 - 7988 (1994)
Styrene and diazo esters react in the presence of copper(II) trifluoromethanesulfonate (1 molpercent) and (1S,2S)-N,N'-di(mesitylmethyl)-1,2-diphenyl-1,2-ethanediamine (2-3 molpercent) to give 2-phenyl-1-cyclopropanecarboxylates in good to excellent optical yields.This reaction has been applied to the synthesis of crythanthemic acid.
Controllable stereoinversion in DNA-catalyzed olefin cyclopropanationviacofactor modification
Cheng, Yu,Hao, Jingya,Jia, Guoqing,Li, Can,Lu, Shengmei,Miao, Wenhui
, p. 7918 - 7923 (2021/06/16)
The assembly of DNA with metal-complex cofactors can form promising biocatalysts for asymmetric reactions, although catalytic performance is typically limited by low enantioselectivities and stereo-control remains a challenge. Here, we engineer G-quadruplex-based DNA biocatalysts for an asymmetric cyclopropanation reaction, achieving enantiomeric excess (eetrans) values of up to +91% with controllable stereoinversion, where the enantioselectivity switches to ?72% eetransthrough modification of the Fe-porphyrin cofactor. Complementary circular dichroism, nuclear magnetic resonance, and fluorescence titration experiments show that the porphyrin ligand of the cofactor participates in the regulation of the catalytic enantioselectivityviaa synergetic effect with DNA residues at the active site. These findings underline the important role of cofactor modification in DNA catalysis and thus pave the way for the rational engineering of DNA-based biocatalysts.
Highly Enantioselective Intermolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]: Solvent Dependency of the Enantioselection
Kitagaki, Shinji,Matsuda, Hideo,Watanabe, Nobuhide,Hashimoto, Shun-Ichi
, p. 1171 - 1174 (2007/10/03)
The enantioselectivity in cyclopropanations catalyzed by dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] has been found to be substantially improved by employing ether as the rarely used solvent. Cyclopropanations of styrenes or 1,1-disubstituted alkenes with 2,4-dimethyl-3-pentyl diazoacetate in ether are promoted by this catalyst to afford the corresponding cyclopropane products in the highest levels of enantioselectivity (up to 98% ee) reported to date for the dirhodium(II)-catalyzed intermolecular cyclopropanation reactions.
Dirhodium(II)tetrakis[3(S)-phthalimido-2-piperidinonate]: A novel dirhodium(II) carboxamidate catalyst for asymmetric cyclopropanation
Watanabe, Nobuhide,Matsuda, Hideo,Kuribayashi, Harumi,Hashimoto, Shun-Ichi
, p. 537 - 542 (2007/10/03)
Dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] catalyzes cyclopropanation of α-methylstyrene with d-menthyl diazoacetate to give d-menthyl (1S,2S)-2-methyl-2-phenylcyclopropanecarboxylate of 90% de.
