798545-62-7Relevant academic research and scientific papers
Organocatalyzed aldol reaction between pyridine-2-carbaldehydes and α-ketoacids: A straightforward route towards indolizidines and isotetronic acids
Liautard, Virginie,Jardel, Damien,Davies, Clotilde,Berlande, Muriel,Buffeteau, Thierry,Cavagnat, Dominique,Robert, Frederic,Vincent, Jean-Marc,Landais, Yannick
, p. 14532 - 14539 (2013)
Enantioselective aldol reactions between substituted pyridine carbaldehydes and α-ketoacids were shown to provide isotetronic acids or their corresponding pyridinium salts, depending on the nature of the substituents on the pyridine ring. The pyridinium salts were generated through nucleophilic attack of the pyridine nitrogen atom onto the reactive keto functional group. Moderate-to-good yields of both compounds were typically obtained and high levels of enantioselectivity were observed by using benzimidazole pyrrolidine I as a catalyst. Hydrogenation of the resulting pyridinium salts led to new indolizidines with high ee values and diastereocontrol. X-ray diffraction studies allowed the determination of the relative configuration of the products. Finally, DFT calculations were performed to rationalize the divergent pathway as a function of the pyridine substituents. BIPpity boppity boo: Asymmetric aldol reactions between pyridine carbaldehydes and α-ketoacids were shown to provide isotetronic acids or their corresponding pyridinium salts with high enantioselectivities by using benzimidazole pyrrolidine (BIP) as a catalyst. Hydrogenation of the resulting pyridinium salts led to new indolizidines with high enantioselectivity and diasterocontrol (see scheme). Copyright
Benzimidazole-pyrrolidine/H+ (BIP/H+), a highly reactive organocatalyst for asymmetric processes
Lacoste, Eric,Vaique, Emilie,Berlande, Muriel,Pianet, Isabelle,Vincent, Jean-Marc,Landais, Yannick
, p. 167 - 177 (2007/10/03)
A new chiral benzimidazole-pyrrolidine has been devised, which exhibits excellent activities in aminocatalyzed aldol reactions, leading to aldol products in high yields and enantioselectivities in the presence of an equimolar amount of a Broensted acid. This organocatalyst has demonstrated remarkable reactivities in aldol processes even with equimolar amounts of aldehyde and ketone in THF. A discussion of the role of the Broensted acid as a co-catalyst is provided along with some applications of this new class of organocatalyst in Robinson annelation and α-amination processes. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Benzoimidazole-pyrrolidine (BIP), a highly reactive chiral organocatalyst for aldol process
Lacoste, Eric,Landais, Yannick,Schenk, Kurt,Verlhac, Jean-Baptiste,Vincent, Jean-Marc
, p. 8035 - 8038 (2007/10/03)
A new chiral benzoimidazole-pyrrolidine ligand (BIP) was shown to catalyze an aldol process in the presence of an equimolar amount of a Br?nsted acid, leading to the aldol adduct in high yield and enantioselectivity. Remarkably, the aldol reaction was sti
