291273-65-9Relevant academic research and scientific papers
Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide
Hatano, Manabu,Yamakawa, Katsuya,Kawai, Tomoaki,Horibe, Takahiro,Ishihara, Kazuaki
, p. 4021 - 4025 (2016)
A highly enantioselective cyanosilylation of ketones was developed by using a chiral lithium(I) phosphoryl phenoxide aqua complex as an acid/base cooperative catalyst. The pentacoordinate silicate generated in situ from Me3SiCN/LiCN acts as an extremely reactive cyano reagent. Described is a 30 gram scale reaction and the synthesis of the key precursor to (+)-13-hydroxyisocyclocelabenzine.
Enantioselective cyanosilylation of ketones with amino acid/BINAP/ ruthenium(II)-lithium phenoxide catalyst systems
Uemura, Masato,Kurono, Nobuhito,Sakai, Yusuke,Ohkuma, Takeshi
supporting information; experimental part, p. 2023 - 2030 (2012/10/23)
Enantioselective reactions of simple ketones, α,α- and β,β-dialkoxy ketones, and α-alkoxy ketones with trimethylsilyl cyanide catalyzed by the bimetallic systems of amino acid/BINAP/ruthenium(II) complexes and lithium phenoxide have been studied [BINAP=2,
Highly enantioselective cyanosilylation of ketones catalyzed by a bifunctional Ti(IV) complex
Shen, Ke,Liu, Xiaohua,Li, Qinghan,Feng, Xiaoming
, p. 147 - 153 (2008/03/28)
A bifunctional catalyst system composed of (S)-prolinamide (2a), titanium(IV) isopropoxide, and phenolic N-oxide (3f) exhibited high catalytic efficiency in the enantioselective cyanosilylation of ketones. In the presence of 2.5 mol % catalyst, a variety
Enantioselective cyanosilylation of ketones catalyzed by a chiral oxazaborolidinium ion
Do, Hyun Ryu,Corey
, p. 5384 - 5387 (2007/10/03)
The chiral oxazaborolidinium salt 1 (X = TfO) is an excellent catalyst for the cyanosilylation of methyl ketones promoted by trimethylsilyl cyanide and diphenylmethyl phosphine oxide as co-reactants (to generate Ph 2MePOTMS(N=C:) as a reactive
Catalytic enantioselective cyanosilylation of ketones: Improvement of enantioselectivity and catalyst turn-over by ligand tuning
Hamashima, Yoshitaka,Kanai, Motomu,Shibasaki, Masakatsu
, p. 691 - 694 (2007/10/03)
Sterical and electronical tuning of the bifunctional catalyst 1 afforded the improved catalyst 2, which promoted the cyanosilylation of ketones with higher enantioselectivity as well as with improved catalyst turn-over with a factor of up to 10. Thus, chiral quaternary α-hydroxynitriles were obtained with excellent ee (up to 94% ee) using 1 mol% of 2 in the case of aryl ketones and 2.5 mol% of 2 in the case of aliphatic ketones.
