Synthesis of enantiopure N-protected 4,5-disubstituted 3-pyrrolidinones and N-protected 2,5-disubstituted 3-pyrrolidinones via the Dieckmann reactionof dicarbonyl compounds derived from enantiopure beta-amino esters

Authors
Wang, Y Ma, DW
Citation
Y. Wang et Dw. Ma, Synthesis of enantiopure N-protected 4,5-disubstituted 3-pyrrolidinones and N-protected 2,5-disubstituted 3-pyrrolidinones via the Dieckmann reactionof dicarbonyl compounds derived from enantiopure beta-amino esters, TETRAHEDR-A, 12(5), 2001, pp. 725-730
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
5
Year of publication
2001
Pages
725 - 730
Database
ISI
SICI code
0957-4166(20010402)12:5<725:SOEN43>2.0.ZU;2-O
Abstract
Under the action of KHMDS in THF solvent the Dieckmann reaction of dicarbon yl compounds derived from enantiopure beta -amino esters provides enantiopu re N-protected 4,5-disubstituted 3-pyrrolidinones, whereas N-protected 2,5- disubstituted 3-pyrrolidinones formed in reactions mediated by tert-BuOK in DMF or toluene. Reduction of these pyrrolidinones afforded enantiopure pol ysubstituted pyrrolidines. (C) 2001 Elsevier Science Ltd. All rights reserv ed.