Zheng J, Wang S.-B, Zheng C, You S.-L * Shanghai Institute of Organic Chemistry, P.
R. of China
Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp
2)–H Functionalization/Annulation Reaction.
J. Am. Chem. Soc. 2015;
137: 4880-4883
Key words
dearomatization - C–H bond activation - rhodium
Significance
Recent efforts have been extended towards the development of asymmetric C–H functionalization
reactions. The authors report an asymmetric version of the previously known metal-catalyzed
dearomatization of phenols.
Comment
Twenty-six dearomatized products were synthesized in moderate to high enantioselectivity
by using a chiral ligand recently invented by Cramer. The use of unsymmetrical alkynes
leads to regioisomeric alkene mixtures in greater than 7:1 selectivity. A primary
deuterium kinetic isotope effect indicates that C–H bond cleavage is most likely the
rate-determining step.
