Enantioselective Desymmetrization of Prochiral Cyclopentene-1,3-diones Triggered by Remote C(sp2)-N Bond Formation
Ashok Donthoju1,2, Lakshmi Revati Magham1,2, Neetu Singh1,2
1Department of Organic Synthesis and Process Chemistry , CSIR-Indian Institute of Chemical Technology (CSIR-IICT) , Hyderabad 500007 , India.
Abstract:
The enantioselective desymmetrization via remote C(sp2)-H amidation of the prochiral 2,2-disubstituted cyclopentene-1,3-dione with N-methoxybenzamide has been developed. The overall process was catalyzed by a chiral bifunctional thiourea catalyst through a sequential conjugate-addition-elimination-tautomerization. This strategy provides rapid access to highly functionalized five-membered carbocycles, bearing an all-carbon quaternary stereogenic center through remote stereocontrol in high yields with moderate to excellent enantioselectivities.
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