10.1021/cs400591u.s001
Dan Huang
Dan
Huang
Xuejian Li
Xuejian
Li
Fangxi Xu
Fangxi
Xu
Luhang Li
Luhang
Li
Xufeng Lin
Xufeng
Lin
Highly Enantioselective Synthesis of Dihydroquinazolinones
Catalyzed by SPINOL-Phosphoric Acids
American Chemical Society
2016
sequence
Dihydroquinazolinones Catalyzed
AcidsThe
spirocyclic
acid
cascade reactions
aldehyde
ortho substituent
dihydroquinazolinone
ee
aminobenzamide
condensation
chiral
stereocontrol
yield
enantioselective organocatalyst
room temperature
Enantioselective Synthesis
2016-02-18 17:59:39
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Highly_Enantioselective_Synthesis_of_Dihydroquinazolinones_Catalyzed_by_SPINOL_Phosphoric_Acids/2369965
The asymmetric condensation/amine
addition cascade sequence of
2-aminobenzamides and aldehydes catalyzed by chiral spirocyclic SPINOL-phosphoric
acids was realized. SPINOL-phosphoric acid <b>1j</b> 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.