cs400591u_si_001.pdf (1.84 MB)
Highly Enantioselective Synthesis of Dihydroquinazolinones Catalyzed by SPINOL-Phosphoric Acids
journal contribution
posted on 2016-02-18, 17:59 authored by Dan Huang, Xuejian Li, Fangxi Xu, Luhang Li, Xufeng LinThe asymmetric condensation/amine
addition cascade sequence of
2-aminobenzamides and aldehydes catalyzed by chiral spirocyclic SPINOL-phosphoric
acids was realized. SPINOL-phosphoric acid 1j was found
to be a general, highly enantioselective organocatalyst for such cascade
reactions at room temperature, affording 2,3-dihydroquinazolinones
in excellent yields (up to 99%) with good to excellent ee’s
(up to 98%). The best level of stereocontrol was obtained for aromatic
aldehydes with an ortho substituent.