1208117-83-2Relevant articles and documents
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.
Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
Yasui, Yoshizumi,Kamisaki, Haruhi,Ishida, Takayuki,Takemoto, Yoshiji
supporting information; experimental part, p. 1980 - 1989 (2010/04/24)
The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)3 showed a remarkable eff
