824938-80-9Relevant articles and documents
Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes
Rombola, Michael,Sumaria, Chintan S.,Montgomery, Thomas D.,Rawal, Viresh H.
, p. 5297 - 5300 (2017)
We report a general method for the synthesis of chiral thiosquaramides, a class of bifunctional catalysts not previously described in the literature. Thiosquaramides are found to be more acidic and significantly more soluble in nonpolar solvents than their oxosquaramide counterparts, and they are excellent catalysts for the unreported, enantioselective conjugate addition reaction of the barbituric acid pharmacaphore to nitroalkenes, delivering the chiral barbiturate derivatives in high yields and high enantioselectivities, even with catalyst loadings as low as 0.05 mol%.
Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification
Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 116 - 120 (2018/12/05)
An asymmetric cyanation of acylsilanes involving the in-situ formation of chiral acylsilane cyanohydrins followed by their kinetic resolution via organocatalytic cycloetherification is described. The highly enantio- and diastereoselective cycloetherificat
Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: Possible route to the 4-methylpregabalin core structure
Vargová, Denisa,Baran, Rastislav,?ebesta, Radovan
supporting information, p. 553 - 559 (2018/03/21)
Chiral derivatives of γ-aminobutyric acid are widely used as medicines and can be obtained by organocatalytic Michael additions. We show here the stereoselective synthesis of 4-methylpregabalin stereoisomers using a Michael addition of dimethyl malonate to a racemic nitroalkene. The key step of the synthesis operates as a kinetic resolution with a chiral squaramide catalyst. Furthermore, specific organocatalysts can provide respective stereoisomers of the key Michael adduct in up to 99:1 er.