6625-66-7Relevant academic research and scientific papers
Enantioselective synthesis of 1-aminoindene derivativesviaasymmetric Br?nsted acid catalysis
Wu, Xiang,Ding, Du,Zhang, Ying,Jiang, Hua-Jie,Wang, Tao,Zhao, Li-Ping
supporting information, p. 9680 - 9683 (2021/09/30)
We describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiralN-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline.
A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes
Deng, Ruohan,Engle, Keary M.,Erbay, Tu??e G.,Li, Zi-Qi,Liu, Peng,Oxtoby, Lucas J.,Tran, Van T.
supporting information, p. 8885 - 8890 (2020/04/15)
Metal-coordinating directing groups have seen extensive use in the field of transition-metal-catalyzed alkene functionalization; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in asymmetric organocatalysis, where reactions rely on reversible covalent interactions between an organic substrate and a chiral mediator, we have developed a transient-directing-group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of a commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.
