Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 72, Pages 18033-18038Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103254
Keywords
annulations; antibiotics; asymmetric catalysis; lawsone; ppm-level catalysis
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Funding
- Department of Science and Technology (DST), SERB, New Delhi [CRG/2018/000775]
- UoH-IoE grant [UoH/IoE/RC1/RC1-20-002]
- University Grants Commission (UGC), New Delhi
- Council of Scientific and Industrial Research (CSIR), New Delhi
- University Grants Commission (UGC)-Dr. D. S. Kothari Postdoctoral Fellowship (DSKPDF) Scheme, New Delhi
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3-Alkyl-lawsones selectively reacted with alpha-alkyl-nitroethylenes under 500 ppm quinine-NH-thiourea catalysis to produce chiral methanobenzo[7]annulenes with high ee, dr, and TON values. These asymmetric, ppm-level catalytic tandem [3+2]-annulations could inspire the design of more ppm-level organocatalytic reactions, while the final molecules serve as basic skeletons of antibiotics.
3-Alkyl-lawsones selectively reacted with alpha-alkyl-nitroethylenes under 500 parts-per-million (ppm) quinine-NH-thiourea-catalysis to furnish the chiral methanobenzo[7]annulenes in up to >99 % ee with >20 : 1 dr and TON up to 1820 through tandem Michael/Henry [3+2]-annulations. These asymmetric ppm-level, catalytic tandem [3+2]-annulations would be highly inspirational for the design of many more ppm-level organocatalytic reactions, and at the same time these final molecules are basic skeletons of antibiotics.
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