Enantioselective Formal C(sp2)−H Vinylation |
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Authors: | Dr. Madhu Sudan Manna Rahul Sarkar Prof. Dr. Santanu Mukherjee |
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Affiliation: | Department of Organic Chemistry, Indian Institute of Science, Bangalore, India |
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Abstract: | An enantioselective formal C(sp2)?H vinylation of prochiral 2,2‐disubstituted cyclopentene‐1,3‐dione is presented. This vinylative desymmetrization is realized by using a two‐step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene‐1,3‐dione and a base‐mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five‐membered carbocycles containing a remote all‐carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities. |
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Keywords: | C− H functionalization decarboxylation desymmetrization lactones vinylation |
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