Electrochemical oxidation of (R)-4-hydroxy-2-pyrrolidone: A key building block for stereoselective N-acyliminium ion coupling reactions

Citation
M. Lennartz et al., Electrochemical oxidation of (R)-4-hydroxy-2-pyrrolidone: A key building block for stereoselective N-acyliminium ion coupling reactions, TETRAHEDRON, 55(50), 1999, pp. 14407-14420
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
50
Year of publication
1999
Pages
14407 - 14420
Database
ISI
SICI code
0040-4020(199912)55:50<14407:EOO(AK>2.0.ZU;2-H
Abstract
The 5-methoxylation of (R)-4-hydroxy-2-pyrrolidone can be performed success fully by direct electrochemical oxidation at 40 mA/cm(2) in methanol at gra phite electrodes using an undivided cell and sodium benzene sulfonate as su pporting electrolyte. After direct protection of the intermediate as TBDMS ether, (4R)-4-tert-butyldimethylsilyloxy-5-methoxy-2-pyrrolidone 3 can be u sed in various diastereoselective amidoalkylation reactions. In most cases cis-stereoselectivity is observed. However, the favored cis-addition may be typical only for Si-organic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.