208844-40-0Relevant academic research and scientific papers
Stereoselective synthesis of 5-(1-hydroxyalkyl)-2-pyrrolidinones utilizing oxidation of 5-alkylidene-2-pyrrolidinones to acyliminium ion precursors
Koseki, Yuji,Kusano, Shuichi,Ichi, Daisuke,Yoshida, Keiji,Nagasaka, Tatsuo
, p. 8855 - 8865 (2000)
A general method was devised for the LiN(TMS)2/AgOTf (=2:1)-catalyzed intramolecular (5-exo-dig) cyclization of β-alkynylamides 1 possessing alkyl, aryl or no functional groups at the terminal alkynes, to 5-alkylidene-2-pyrrolidinones 2. These 5-alkylidene-2-pyrrolidinones were oxidized to the diol-type alkoxylactams 3 by dimethyldioxirane (DMD) or mCPBA in MeOH. These alkoxylactams are useful as tertiary N-acyliminium ion precursors for the synthesis of threo-5-(1-hydroxyalkyl)-2-pyrrolidinone derivatives 5. (C) 2000 Elsevier Science Ltd.
