Linked Life Data

7742175

Source:http://linkedlifedata.com/resource/pubmed/id/7742175

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
1995-6-9
pubmed:abstractText
The diastereofacial selectivity of both inter- and intramolecular Diels-Alder reactions with dienes having an allylic stereogenic center has been studied by varying the allylic oxygen protective group. Four different hydroxy protective groups were investigated including benzyl, t-butyldiphenylsilyl, triethylsilyl, and t-butyldimethylsilyl ethers. For inter-molecular reactions, the benzyl ether derivative gave the highest pi-facial selectivity through a transition state in which the allylic stereocenter favors the CH eclipsed conformation. For intramolecular cycloadditions, the t-butyldimethylsilyl group gave a slightly higher selectivity than the benzyl ether derivative through a transition state in which the allylic stereocenter favors the CO eclipsed conformation. The opposite diastereofacial selectivity observed for inter- and intramolecular reactions is explained by considering both steric and electronic effects.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
0899-0042
pubmed:author
pubmed:issnType
Print
pubmed:volume
7
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
96-102
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1995
pubmed:articleTitle
The influence of protective groups on diastereofacial selectivity of Diels-Alder cycloaddition reactions.
pubmed:affiliation
Department of Chemistry, Miami University, Oxford, OH 45056, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S., Research Support, Non-U.S. Gov't