Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 42, Pages 14912-14919Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602253
Keywords
C-H functionalization; decarboxylation; desymmetrization; lactones; vinylation
Categories
Funding
- SERB [SB/S1/OC-63/2013]
- CSIR [02(0207)/14/EMR-II]
- DAE-BRNS [2013/37C/56/BRNS/2440]
- CSIR
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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.
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