Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 5, Pages 995-1000Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801453
Keywords
coumarin; organic catalysis; synthetic method; Meldrum's acid; decarboxylative protonation
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Funding
- INSA Rouen, Rouen University, CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- region Normandie (CRUNCh network)
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C5-disubstituted Meldrum's acid precursors were shown to be a useful platform for the synthesis of an array of 3-alkylated dihydrocoumarins with up to 93:7 er, thanks to an enantioselective domino cyclization-decarboxylative-protonation reaction triggered by an unprecedented benzhydryl-derived cupreine organocatalyst. This cyclization sequence was extended to an emerging organocatalytic decarboxylative-chlorination reaction in the presence of trichloroquinolinone and by means of a bifunctional cinchona derived Bronsted base which gave rise to the formation of dihydrocoumarins (up to 79:21 er) with a tertiary chlorinated stereocenter.
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