Tetrahedron

Stereoselective synthesis of 5-(1-hydroxyalkyl)-2-pyrrolidinones utilizing oxidation of 5-alkylidene-2-pyrrolidinones to acyliminium ion precursors

Y Koseki, S Kusano, D Ichi, K Yoshida, T Nagasaka

Index: Koseki, Yuji; Kusano, Shuichi; Ichi, Daisuke; Yoshida, Keiji; Nagasaka, Tatsuo Tetrahedron, 2000 , vol. 56, # 45 p. 8855 - 8865

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Citation Number: 43

Abstract

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 ...