Journal
ORGANIC LETTERS
Volume 12, Issue 5, Pages 952-955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902949d
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- University of Minnesota (UMN)
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The first asymmetric cyanoamidation with synthetically useful enantioselectivity (ee up to 99%) to produce 3,3-disubstituted oxindoles is reported. Palladium catalysts with chiral phosphoramidite ligands activate the cyanoformamide C-CN bond, which is subsequently functionalized with a tethered alkene to give all-carbon quaternary stereocenters. The use of the N,N-(i-Pr)(2) derivative of octahydro-MonoPhos allowed the production of oxindoles with high enantioselectivities, Cyanoformamides bearing free N-H groups are now tolerated, potentially allowing protecting-group-free synthesis. Oxindole products of cyanoamidation are rapidly transformed into (+)-horsfiline, (-)-coerulescine, and (-)-esermethole.
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