| dc.contributor.author |
Koulocheri, SD |
en |
| dc.contributor.author |
Magiatis, P |
en |
| dc.contributor.author |
Skaltsounis, A-L |
en |
| dc.contributor.author |
Haroutounian, SA |
en |
| dc.date.accessioned |
2014-06-06T06:44:21Z |
|
| dc.date.available |
2014-06-06T06:44:21Z |
|
| dc.date.issued |
2000 |
en |
| dc.identifier.issn |
00404020 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/1820 |
|
| dc.relation.uri |
http://www.scopus.com/inward/record.url?eid=2-s2.0-0034637612&partnerID=40&md5=aa8e7f1c9106f0d967a60700e03dcf90 |
en |
| dc.subject |
Amino acid |
en |
| dc.subject |
Azasugar |
en |
| dc.subject |
Hydrazoic acid |
en |
| dc.subject |
Michael addition |
en |
| dc.subject |
Thiophenol |
en |
| dc.subject.other |
amino acid |
en |
| dc.subject.other |
carbohydrate derivative |
en |
| dc.subject.other |
heterocyclic compound |
en |
| dc.subject.other |
hydroxymethyl dihydropyridone |
en |
| dc.subject.other |
pyridone derivative |
en |
| dc.subject.other |
thiophenol |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
chirality |
en |
| dc.subject.other |
derivatization |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
enzyme inhibition |
en |
| dc.subject.other |
Michaelis Menten kinetics |
en |
| dc.subject.other |
priority journal |
en |
| dc.subject.other |
proton nuclear magnetic resonance |
en |
| dc.subject.other |
spectroscopy |
en |
| dc.subject.other |
stereochemistry |
en |
| dc.title |
Stereoselective Michael addition of thiophenols, amino acids and hydrazoic acid to (2S)-hydroxymethyl-dihydropyridone as a convenient route to novel azasugar derivatives |
en |
| heal.type |
journalArticle |
en |
| heal.publicationDate |
2000 |
en |
| heal.abstract |
The outcome and stereochemical aspects of 1,4-conjugate addition of thiophenols, α-aminoacid derivatives and hydrazoic acid to chiral (2S)-hydroxymethyl-dihydropyridone 3 is presented. Subsequent reduction with NaBH4 provided predominantly the kinetically favored axial 3-piperidinol adducts. The stereochemistry of the products, which depends on electrostatic interaction and steric hindrance, was revealed by 1H NMR and 2D NOESY spectroscopic analysis. (C) 2000 Elsevier Science Ltd. |
en |
| heal.journalName |
Tetrahedron |
en |
| dc.identifier.issue |
33 |
en |
| dc.identifier.volume |
56 |
en |
| dc.identifier.spage |
6135 |
en |
| dc.identifier.epage |
6141 |
en |