27640-33-1Relevant articles and documents
SYNTHESIS OF PYRROLIZIDINES AND RELATED COMPOUNDS BY ALDOL CYCLIZATION OF N--α-AMINOALDEHYDES
Ikeda, Masazumi,Harada, Suzumi,Yamasaki, Atsuko,Kinouchi, Katsuko,Ishibashi, Hiroyuki
, p. 943 - 954 (1988)
Treatment of 1--2-pyrrolidinecarbaldehyde with sodium hydride in tetrahydrofuran (THF) gave the aldol condensation product, 5,6,7,7a-tetrahydro-2-methylthio-3H-pyrrolizin-3-one.However, when the same aldehyde was treated with sodium hydroxide in aqueous THF, 5,6,7,7a-tetrahydro-7a-hydroxy-3-methylthio-3H-pyrrolizin-3-one was obtained.These reactions were applied to the synthesis of indolizidine and pyrroloindole derivatives.
Design and synthesis of novel indoline-(thio)urea hybrids
Lafzi, Ferruh,Kilic, Haydar,Tanriver, Gamze,Avc?, ?yküm Naz,Catak, Saron,Saracoglu, Nurullah
supporting information, p. 3510 - 3527 (2019/11/14)
A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.
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.