1115-12-4Relevant articles and documents
Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes
Rondla, Naveen R.,Levi, Samuel M.,Ryss, Jonathan M.,Berg, Rachel A. Vanden,Douglas, Christopher J.
supporting information; experimental part, p. 1940 - 1943 (2011/06/17)
Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents m
Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole
Reddy, Venkata Jaganmohan,Douglas, Christopher J.
supporting information; experimental part, p. 952 - 955 (2010/06/15)
(Figure Presented) The first asymmetric cyanoamidation with synthetically useful enantioselectivlty (ee up to 99%) to produce 3,3-disubstltuted oxindoles Is reported. Palladium catalysts with chi ral phosphoramldite 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 enantioselectivlties. 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.
Enantioselective synthesis of 3,3-disubstituted oxindoles through pd-catalyzed cyanoamidation
Yasui, Yoshizumi,Kamisaki, Haruhi,Takemoto, Yoshiji
supporting information; experimental part, p. 3303 - 3306 (2009/05/07)
(Chemical Equation Presented) The first enantioselective cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)2, an optically active phosphoramidite, and N,N-dimethylpropylene urea (DMPU) i