Linked Life Data

18729322

Source:http://linkedlifedata.com/resource/pubmed/id/18729322

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
18
pubmed:dateCreated
2008-9-15
pubmed:abstractText
Azabicyclo[4.3.0]nonanes were assembled, from chiral allylsilanes possessing an oxime moiety, using a stereocontrolled formal [2 + 2 + 2] radical-ionic process. The cascade involves the addition of an alpha-iodoester to the less substituted end of the enoxime which is then followed by a 5-exo-trig cyclization onto the aldoxime function, producing an alkoxyaminyl radical species which finally lactamizes to afford the titled piperidinone. High levels of stereoinduction were observed, demonstrating the ability of a silicon group located at the allylic position to efficiently control the stereochemistry of the two newly created stereogenic centers. When the radical cascade was extended to ketoximes, the resulting sterically hindered alkoxyaminyl radical did not react further with the initiator Et3B to produce the expected nucleophilic amidoborane complex. In sharp contrast, this long-lived radical recombined with the initial alpha-stabilized ester radical to produce a cyclopentane incorporating two ester fragments.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
19
pubmed:volume
73
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
6983-93
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Synthesis of fused piperidinones through a radical-ionic cascade.
pubmed:affiliation
University Bordeaux 1, Institut des Sciences Moléculaires, UMR-CNRS 5255, 351, Cours de la Libération, F-33405 Talence Cedex, France.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't