1343404-40-9Relevant academic research and scientific papers
Synthesis, characterisation, and organocatalytic activity of chiral tetrathiahelicene diphosphine oxides
Cauteruccio, Silvia,Dova, Davide,Benaglia, Maurizio,Genoni, Andrea,Orlandi, Manuel,Licandro, Emanuela
, p. 2694 - 2702 (2014/05/06)
Two new chiral tetrathia[7]helicene (7-TH) based tertiary phosphine oxides (±)-2b and (±)-2c, bearing two substituents on the phosphorus atoms with different steric and electronic properties, have been synthesised and fully characterised by means of analytical and spectroscopic techniques. The resolution of (±)-2a-c into their antipodes was accomplished by HPLC separation on a chiral stationary phase, and their chiroptical properties were investigated by CD spectroscopy. The behaviour of 2a-c as organocatalysts was assessed in representative reactions mediated by tri- or tetrachlorosilane. 7-TH-based phosphine oxides 2a and 2b promoted both ketoimine reduction and stereoselective carbon-carbon bond formation in good chemical yields and diastereoselectivity, albeit with low enantioselectivity, thus opening the way to the development of a novel class of enantiopure helical-based phosphorus organocatalysts. A novel class of tetrathia[7]helicene-based diphosphine oxides has been synthesised, and their catalytic behaviour as chiral helical phosphorus Lewis bases has been preliminary investigated in organocatalytic reactions. Copyright
Tetrathiaheterohelicene phosphanes as helical-shaped chiral ligands for catalysis
Monteforte, Marco,Cauteruccio, Silvia,Maiorana, Stefano,Benincori, Tiziana,Forni, Alessandra,Raimondi, Laura,Graiff, Claudia,Tiripicchio, Antonio,Stephenson, G. Richard,Licandro, Emanuela
, p. 5649 - 5658 (2011/11/29)
Tetrathia[7]helicene-based phosphanes thiaheliphos (2a), nPr-thiaheliphos (2b) and di-nPr-thiaheliphos (2c) have been prepared from the 2,13-dilithio derivatives of thiahelicenes 1a-c by reaction with an excess of Ph 2PCl. Protection of the air
