Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 16, Pages 6037-6041Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500710
Keywords
asymmetric catalysis; enantioselectivity; organocatalysis; quinone methides; sulfones
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Funding
- University of Bologna (RFO)
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A new approach to the utilization of highly reactive and unstable ortho-quinone methides (o-QMs) in catalytic asymmetric settings is presented. The enantioselective reactions are catalysed by bifunctional organocatalysts, and the o-QM intermediates are formed in situ from 2-sulfonylalkyl phenols through base-promoted elimination of sulfinic acid. The use of mild BrOnsted basic conditions for transiently generating o-QMs in catalytic asymmetric processes is unprecedented, and allows engaging productively in the reactions nucleophiles such as Meldrum's acid, malononitrile and 1,3-dicarbonyls. The catalytic transformations give new and general entries to 3,4-dihydrocoumarins, 4H-chromenes and xanthenones. These frameworks are recurring structures in natural product and medicinal chemistry, as testified by the formal syntheses of (R)-tolterodine and (S)-4-methoxydalbergione from the catalytic adducts.
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