ENANTIOSELECTIVE, ELECTROCATALYTIC LACTONIZATION OF METHYL-SUBSTITUTED DIOLS ON A TEMPO-MODIFIED GRAPHITE FELT ELECTRODE IN THE PRESENCE OF(-)-SPARTEINE

Authors
YANAGISAWA Y KASHIWAGI Y KURASHIMA F ANZAI J OSA T BOBBITT JM
Citation
Y. Yanagisawa et al., ENANTIOSELECTIVE, ELECTROCATALYTIC LACTONIZATION OF METHYL-SUBSTITUTED DIOLS ON A TEMPO-MODIFIED GRAPHITE FELT ELECTRODE IN THE PRESENCE OF(-)-SPARTEINE, Chemistry Letters, (12), 1996, pp. 1043-1044
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
12
Year of publication
1996
Pages
1043 - 1044
Database
ISI
SICI code
0366-7022(1996):12<1043:EELOM>2.0.ZU;2-7
Abstract
A TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxyl)graphite felt electrode afforded enantioselective, electrocatalytic lactonized products of (S )-(-)-3,4,5,6-tetrahydro-4-methyl-2-pyranone, (S)-(-)-4,5-dihydro-4-me thyl-2(3H)-furano and (S)(-)-4,5-dihydro-5-methyl-2(3H)-furanone from 3-methylpentane-1,5-diol, (S)-(-)-2-methylbutane-1,4-diol and racemic pentane-1,4-diol, respectively, in enantiomeric excess more than 95%, in the presence of (-)-sparteine in acetonitrile. The current efficien cy and isolated yield of former two lactones were more than 90%.