rdf:type |
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lifeskim:mentions |
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pubmed:issue |
29
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pubmed:dateCreated |
2010-7-29
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pubmed:abstractText |
A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.
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pubmed:grant |
|
pubmed:commentsCorrections |
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pubmed:language |
eng
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pubmed:journal |
|
pubmed:citationSubset |
IM
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pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Jul
|
pubmed:issn |
1520-5126
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pubmed:author |
|
pubmed:issnType |
Electronic
|
pubmed:day |
28
|
pubmed:volume |
132
|
pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
10015-7
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pubmed:dateRevised |
2011-11-17
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pubmed:meshHeading |
|
pubmed:year |
2010
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pubmed:articleTitle |
Enantioselective organo-SOMO cascade cycloadditions: a rapid approach to molecular complexity from simple aldehydes and olefins.
|
pubmed:affiliation |
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
|