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Enantioselective Formal C(sp(2))-H Vinylation

Manna, Madhu Sudan and Sarkar, Rahul and Mukherjee, Santanu (2016) Enantioselective Formal C(sp(2))-H Vinylation. In: CHEMISTRY-A EUROPEAN JOURNAL, 22 (42). pp. 14912-14919.

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Official URL: http://dx.doi.org/10.1002/chem.201602253


An enantioselective formal C(sp(2))-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 decar-boxylation. 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.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Dec 2016 06:23
Last Modified: 03 Dec 2016 06:23
URI: http://eprints.iisc.ac.in/id/eprint/55272

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