rdf:type |
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lifeskim:mentions |
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pubmed:issue |
28
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pubmed:dateCreated |
2002-7-10
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pubmed:abstractText |
An efficient and highly enantioselective (>/=92% ee) catalytic method for conjugate addition of alkylzinc reagents to cyclic nitroalkenes is reported. Reactions are promoted in the presence of 0.5-5 mol % (CuOTf)2.C6H6 and 1-10 mol % of chiral amino acid-based phosphine ligands at 0 degrees C in toluene. The Cu-catalyzed reactions can be effectively carried out with small-, medium-, and large-ring nitroalkenes. Depending on the reaction conditions used, either the nitro or the corresponding alpha-substituted ketone product can be readily accessed by the present protocol.
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pubmed:grant |
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Alkenes,
http://linkedlifedata.com/resource/pubmed/chemical/Copper,
http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexanes,
http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexenes,
http://linkedlifedata.com/resource/pubmed/chemical/Hydrocarbons, Cyclic,
http://linkedlifedata.com/resource/pubmed/chemical/Ketones,
http://linkedlifedata.com/resource/pubmed/chemical/Nitro Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Organometallic Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/cyclohexene,
http://linkedlifedata.com/resource/pubmed/chemical/diethylzinc
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pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
0002-7863
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pubmed:author |
|
pubmed:issnType |
Print
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pubmed:day |
17
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pubmed:volume |
124
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
8192-3
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pubmed:dateRevised |
2008-1-17
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pubmed:meshHeading |
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pubmed:year |
2002
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pubmed:articleTitle |
Cu-catalyzed enantioselective conjugate addition of alkylzincs to cyclic nitroalkenes: catalytic asymmetric synthesis of cyclic alpha-substituted ketones.
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pubmed:affiliation |
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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