Journal
CHEMICAL SCIENCE
Volume 2, Issue 7, Pages 1369-1378Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00160d
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Funding
- NIHGMS [RO1 GM073932-05]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM073932] Funding Source: NIH RePORTER
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A racemic Au(I)-catalyzed three-component reaction has been developed to prepare cyclic carbamimidates from imines, terminal alkynes, and sulfonylisocyanates. This reaction exploits the carbophilic p-acidity of gold catalysts to first activate an alkyne toward deprotonation and secondly, to activate the internal alkyne generated toward intramolecular O-cyclization. Unlike similar previously reported multicomponent gold-catalyzed reactions, the stereocenter generated during the alkynylation is preserved in the product. This trait was exploited by developing an enantioselective variant, using an unusual trans-1-diphenylphosphino-2-arylsulfamidocyclohexane ligand. Moderate to excellent levels of enantioselectivity were obtained using a variety of N-arylbenzylidene anilines (41-95% ee, 18 examples).
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