1075721-62-8Relevant articles and documents
Diaminomethylenemalononitrile as a Chiral Single Hydrogen Bond Catalyst: Application to Enantioselective Conjugate Addition of α-Branched Aldehydes
Akutsu, Hiroshi,Hirashima, Shin-ichi,Kawada, Masahiro,Matsumoto, Takashi,Miura, Tsuyoshi,Nakashima, Kosuke,Tsuyusaki, Ryo,Yanai, Hikaru
supporting information, p. 2272 - 2275 (2021/07/16)
An improved diaminomethylenemalononitrile organocatalyst, bearing a N,N-disubstituted structure, promoted enantioselective conjugate addition reaction of α-branched aldehydes with vinyl sulfone, affording adducts with excellent enantioselectivities (up to 96% ee). Mechanistic studies revealed that the diaminomethylenemalononitrile motif holds the vinyl sulfone substrate using a single hydrogen bond accompanied by multiple weak interactions, including electrostatic C?H???O interactions.
Perfluoroalkanesulfonamide organocatalysts for asymmetric conjugate additions of branched aldehydes to vinyl sulfones
Nakashima, Kosuke,Murahashi, Miho,Yuasa, Hiroki,Ina, Mariko,Norihiro, Tada,Itoh, Akichika,Hirashima, Shin-Ichi,Koseki, Yuji,Miura, Tsuyoshi
, p. 14529 - 14542 (2014/01/17)
Asymmetric conjugate additions of branched aldehydes to vinyl sulfones promoted by sulfonamide organocatalyst 6 or 7 have been developed, allowing facile synthesis of the corresponding adducts with all-carbon quaternary stereocenters in excellent yields w
Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds
Quintard, Adrien,Belot, Sebastien,Marchai, Estelle,Alexakis, Alexandre
experimental part, p. 927 - 936 (2010/04/25)
The substitution of the 4-position of hydroxyproline by a phenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the α-functionalization of a wide range of linear/ branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and α-amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.