Linked Life Data

18067312

Source:http://linkedlifedata.com/resource/pubmed/id/18067312

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2007-12-28
pubmed:abstractText
Diels-Alder cycloadditions of dehydroalanine derivatives with cyclopentadiene, applicable to the synthesis of palau'amine, were investigated experimentally and using DFT computations at the B3LYP/6-31G* level of theory. Oxazolone and thiohydantoin dienophiles were found to be significantly more reactive than hydantoins or dehydroalanine methyl esters. The increased reactivity of the thiohydantoins relative to hydantoins is attributed to increased conjugation of nitrogen lone pairs into the thiocarbonyl group. beta-Substitution greatly decelerates the cycloadditions due to steric interactions in the transition states outweighing any electronic activation by chlorine. Hydantoins and thiohydantoins were found to be exo-selective, while the corresponding oxazolones and dehydroalanines were unselective.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
4
pubmed:volume
73
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
102-10
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.
pubmed:affiliation
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC, Canada, H3A 2K6.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't