Source:http://linkedlifedata.com/resource/pubmed/id/19627154
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
32
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pubmed:dateCreated |
2009-9-2
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pubmed:abstractText |
The first enantioselective organocatalytic alpha-nitroalkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
1520-5126
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
19
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pubmed:volume |
131
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
11332-4
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pubmed:meshHeading |
pubmed-meshheading:19627154-Aldehydes,
pubmed-meshheading:19627154-Alkylation,
pubmed-meshheading:19627154-Amines,
pubmed-meshheading:19627154-Amino Acids,
pubmed-meshheading:19627154-Catalysis,
pubmed-meshheading:19627154-Models, Molecular,
pubmed-meshheading:19627154-Molecular Structure,
pubmed-meshheading:19627154-Oxidation-Reduction,
pubmed-meshheading:19627154-Stereoisomerism
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pubmed:year |
2009
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pubmed:articleTitle |
Enantioselective aldehyde alpha-nitroalkylation via oxidative organocatalysis.
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pubmed:affiliation |
Merck Center for Catalysis, 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
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