A NEW CHIRAL LITHIUM AMIDE BASED ON (S)-2-[1-(3,3-DIMETHYL)PYRROLIDINYLMETHYL] PYRROLIDINE - SYNTHESIS, NMR-STUDIES AND USE IN THE ENANTIOSELECTIVE DEPROTONATION OF CYCLOHEXENE OXIDE

Authors
KHAN AZQ DEGROOT RW ARVIDSSON PI DAVIDSSON O
Citation
Azq. Khan et al., A NEW CHIRAL LITHIUM AMIDE BASED ON (S)-2-[1-(3,3-DIMETHYL)PYRROLIDINYLMETHYL] PYRROLIDINE - SYNTHESIS, NMR-STUDIES AND USE IN THE ENANTIOSELECTIVE DEPROTONATION OF CYCLOHEXENE OXIDE, Tetrahedron : asymmetry, 9(7), 1998, pp. 1223-1229
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
7
Year of publication
1998
Pages
1223 - 1229
Database
ISI
SICI code
0957-4166(1998)9:7<1223:ANCLAB>2.0.ZU;2-L
Abstract
A new chiral lithium amide has been designed starting from (S)-proline . This new chiral lithium amide has been used for asymmetric deprotona tion/ring opening of cyclohexene oxide to give (S)-2-cyclohexen-1-ol i n 88% yield and 78% enantiomeric excess. NMR studies of the lithium am ide and the ligand-substrate complex are also presented. (C) 1998 Else vier Science Ltd. All rights reserved.