134452-33-8Relevant academic research and scientific papers
Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents
Soeta, Takahiro,Ishizaka, Tomohiro,Tabatake, Yuta,Ukaji, Yutaka
supporting information, p. 16773 - 16778 (2016/02/18)
Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction. Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee; see scheme). A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.
New chiral ferrocenyl amidophosphine ligand for remarkable improvement of enantioselectivities in copper-catalyzed addition of diethylzinc to N-sulfonylimines
Wang, Min-Can,Xu, Cui-Lian,Zou, Yu-Xi,Liu, Hong-Min,Wang, De-Kun
, p. 5413 - 5416 (2007/10/03)
(S)-N-Ferrocenoyl-2-[(diphenylphosphino)methyl]-pyrrolidine 3 was conveniently prepared from commercially available l-proline and ferrocenecarboxylic acid. In the presence of a catalytic amount of chiral ligand 3 (4 mol %) and Cu(OTf)2 (3 mol %), the asymmetric addition of diethylzinc to N-sulfonylimines was achieved in 57-99% yield with up to 88% ee.
Asymmetric Alkylation of N-Toluenesulfonylimines with Dialkylzinc Reagents Catalyzed by Copper-Chiral Amidophosphine
Soeta, Takahiro,Nagai, Kazushige,Fujihara, Hidetaka,Kuriyama, Masami,Tomioka, Kiyoshi
, p. 9723 - 9727 (2007/10/03)
The synthetic procedure of a chiral amidophosphine ligand 5 bearing two bulky substituents, 2,4,6-trimethylphenylmethyl or 2,4,6-triisopropylphenylmethyl groups, on the pyrrolidine ring was improved by employing the borane-THF reduction of the lactam-alco
An efficient preparation of optically active α-furfuryl amide by kinetic resolution using the modified Sharpless asymmetric epoxidation reagents
Zhou,Lu,Wang
, p. 2641 - 2654 (2007/10/02)
Kinetic resolution of α-furfuryl amide was first carried out by using the modified Sharpless asymmetric epoxidation reagent to give the slow-reacting enantiomers, (S)-1(a-h) and (R)-1(b,f) in high enantioselectivity (90-100% e.e) and high chemical yield (
An efficient preparation of optically active α-furfuryl amide by kinetic resolution using the modified sharpless asymmetric epoxidation reagent
Zhou, Wei-Shan,Lu, Zhi-Hui,Wang, Zhi-Min
, p. 1467 - 1470 (2007/10/02)
Kinetic resolution of α-furfuryl amide was first carried out by using the modified Sharpless asymmetric epoxidation reagent to give the slow-reacting enantiomers, (S)-la-f and (R)-lb,f in high enantioselectivity (90-100% e.e) and high chemical yield (45-5
