Journal
CHEMICAL SCIENCE
Volume 2, Issue 8, Pages 1470-1473Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00176k
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Funding
- NIHGMS [R01 GM078201-05]
- Vietnamese government
- Merck
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM078201] Funding Source: NIH RePORTER
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The intramolecular asymmetric cyclization of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3 pi-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective cyclization with an array of pendent allylsilanes thus efficiently providing a new approach to the construction of five-, six- and seven-membered carbocycles and heterocycles.
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