American Chemical Society
Browse
cs400591u_si_001.pdf (1.84 MB)

Highly Enantioselective Synthesis of Dihydroquinazolinones Catalyzed by SPINOL-Phosphoric Acids

Download (1.84 MB)
journal contribution
posted on 2016-02-18, 17:59 authored by Dan Huang, Xuejian Li, Fangxi Xu, Luhang Li, Xufeng Lin
The 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.

History