Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 41, Pages 13268-13271Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09484
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Funding
- Max-Planck-Society
- European Research Council (Advanced Grant High Performance Lewis Acid Organocatalysis, HIPOCAT)
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A highly enantioselective Bronsted acid catalyzed intramolecular carbonyl-ene reaction of olefinic aldehydes has been developed. Using a confined imidodiphosphate catalyst, the reaction delivers diverse trans-3,4-disubstituted carbo- and heterocyclic five-membered rings in high yields and with good to excellent diastereo- and enantioselectivities. ESI-MS, NMR, and DFT mechanistic studies reveal that the reaction proceeds via a stepwise pathway involving a novel covalent intermediate.
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