112607-27-9Relevant articles and documents
Catalytic, Enantioselective β-Protonation through a Cooperative Activation Strategy
Wang, Michael H.,Barsoum, David,Schwamb, C. Benjamin,Cohen, Daniel T.,Goess, Brian C.,Riedrich, Matthias,Chan, Audrey,Maki, Brooks E.,Mishra, Rama K.,Scheidt, Karl A.
, p. 4689 - 4702 (2017/05/12)
The NHC-catalyzed transformation of unsaturated aldehydes into saturated esters through an organocatalytic homoenolate process has been thoroughly studied. Leveraging a unique “Umpolung”-mediated β-protonation, this process has evolved from a test bed for homoenolate reactivity to a broader platform for asymmetric catalysis. Inspired by our success in using the β-protonation process to generate enals from ynals with good E/Z selectivity, our early studies found that an asymmetric variation of this reaction was not only feasible, but also adaptable to a kinetic resolution of secondary alcohols through NHC-catalyzed acylation. In-depth analysis of this process determined that careful catalyst and solvent pairing is critical for optimal yield and selectivity; proper choice of nonpolar solvent provided improved yield through suppression of an oxidative side reaction, while employment of a cooperative catalytic approach through inclusion of a hydrogen bond donor cocatalyst significantly improved enantioselectivity.
Enantioselective β-Protonation by a Cooperative Catalysis Strategy
Wang, Michael H.,Cohen, Daniel T.,Schwamb, C. Benjamin,Mishra, Rama K.,Scheidt, Karl A.
supporting information, p. 5891 - 5894 (2015/05/27)
An enantioselective N-heterocyclic carbene (NHC)-catalyzed β-protonation through the orchestration of three distinct organocatalysts has been developed. This cooperative catalyst system enhances both yield and selectivity, compared to only the NHC-catalyz
Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand
Ito, Masato,Ootsuka, Takashi,Watari, Ryo,Shiibashi, Akira,Himizu, Akio,Ikariya, Takao
supporting information; experimental part, p. 4240 - 4242 (2011/06/21)
A novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed. Chiral modification in the ligand sphere of the well-defined Cp*Ru catalyst molecule opens up a new possibility for the development of an enantioselective hydrogenation of racemic substrates via dynamic kinetic resolution.