1152500-30-5Relevant articles and documents
Catalytic asymmetric intramolecular hydroarylations of ω-aryloxy- and arylamino-tethered α,β-unsaturated aldehydes
Lu, Hai-Hua,Liu, Hui,Wu, Wei,Wang, Xu-Fan,Lu, Liang-Qiu,Xiao, Wen-Jing
supporting information; scheme or table, p. 2742 - 2746 (2009/12/03)
The first enantioselective organocatalytic intramolecular hydroarylations of phenol and aniline-derived enals were investigated. The proposed method provided an atom economic and straightforward approach to optically active chromans and tetrahydroquinolines in high enantioselectivities and in good yields. The study demonstrated the efficiency of organocatalysis to achieve the first asymmetric intramolecular arylation of ω aryloxy- arylamino-tethered α, and β-unsaturated aldehydes using a chiral secondary amine catalyst. Proposed transformation method resulted in the production of functionalized chromans and tetrahydroquinoline in high enantiopurity. The study also examined the scope of substrates in this organocatalytic reaction using a catalyst 4/p-TsOH.H2O in diethyl ether. The catalyst screening observed a higher yield up to 83% and comparable enantiometric excess up to 88% that can be obtained in a chiral secondary amine employed as the reaction catalyst.
