77210-46-9Relevant academic research and scientific papers
Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
supporting information, p. 5760 - 5764 (2017/05/12)
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Photochemical Reaction of Optically Active 2-(1'-Methylallyl)anilines with Methanol
Scholl, Bernhard,Hansen, Hans-Juergen
, p. 1823 - 1832 (2007/10/02)
It is shown that (-)-(S)-2-(1'-methylallyl)aniline ((-)-(S)-4) on irradiation in methanol yields (-)-(2S,3R)-2,3-dimethylindoline ((-)-trans-8), (-)-(1'R,2'R)-2-(2'-methoxy-1'-methylpropylaniline ((-)-erythro-9) as well as racemic (1'RS,2'SR)-2-(2'-methoxy-1'-methylpropyl)aniline ((+/-)-threo-9) in 27.1, 36.4 and 15.7percent yield, respectively (see Scheme 3).By deamination and chemical correlation with (+)-(2R,3R)-3-phenyl-2-butanol ((+)-erythro-13; see Scheme 4) it was found that (-)-erythro-9 has the same absolute configuration and optical purity as the starting material (-)-(S)-4.Comparable results are obtained when (-)-(S)-N-methyl-2-(1'-methylallyl)aniline ((-)-(S)-7) is irradiated in methanol, i.e. the optically active indoline (+)-trans-10 and the methanol addition product (-)-erythro-11 along with its racemic threo-isomer are formed (cf.Scheme 3).These findings demonstrate that the methanol addition products arise from stereospecific, methanol-induced ring opening of intermediate, chiral trans-(->(-)-erythro-compounds) and achiral cis-spiroocta-4,6-dien-8-imines (->(+/-)-threo-compounds; see Schemes 1 and 2).
