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Synfacts 2015; 11(7): 0721
DOI: 10.1055/s-0034-1380947
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric Dearomatization of Naphthols with Alkynes

Contributor(s):
Mark Lautens
,
Thomas Johnson
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(sp2)–H Functionalization/Annulation Reaction.

J. Am. Chem. Soc. 2015;
137: 4880-4883
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Publication History

Publication Date:
17 June 2015 (online)

 
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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.


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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.


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