86734-19-2Relevant articles and documents
A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes
Dixon, Darren J.,Scott, Mark S.,Luckhurst, Chris A.
, p. 2317 - 2320 (2007/10/03)
A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.
Intramolecular 1,5-hydrogen atom transfer radical reaction of pyrrolidine derivatives
Ishizaki, Miyuki,Takano, Hideaki,Hoshino, Osamu
, p. 305 - 314 (2007/10/03)
Intramolecular 1,5-hydrogen atom transfer radical cyclization reaction of pyrrolidine derivatives was examined. Radical reaction of 3,4-bis(α,β- unsaturated acyloxy)-(8, 9) and 3,4-diacetoxy (13)-N-[(o- halobenzyl)pyrrolidines underwent elimination of two acyloxy groups to give mainly N-benzylpyrrole (11). On the other hand, the similar reaction of 3,4- diallyloxy-N-(o-bromobenzyl)pyrrolidine (16) gave desired hexahydrofuro[3,2- b]pyrroles (17, 18) together with a dimeric hexahydrofuro[3,2-b]pyrrole (19).