Source:http://linkedlifedata.com/resource/pubmed/id/20845958
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
40
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pubmed:dateCreated |
2010-10-7
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pubmed:abstractText |
Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral aldehydes with useful regioselectivity and high enantioselectivity (up to 99% ee). Chiral Roche aldehyde is obtained with 97% ee from the hydroformylation of allyl silyl ethers. Commonly difficult substrates such as 1,1- and 1,2-disubstituted alkenes undergo effective hydroformylation with 89-97% ee and complete conversion for six examples. Palladium-catalyzed aerobic oxidative amination of allyl benzyl ether followed by enantioselective hydroformylation yields the ?(3)-aminoaldehyde with 74% ee.
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pubmed:grant |
http://linkedlifedata.com/resource/pubmed/grant/R01 GM067173-06A1,
http://linkedlifedata.com/resource/pubmed/grant/R01 GM067173-07,
http://linkedlifedata.com/resource/pubmed/grant/R01 GM067173-07S1,
http://linkedlifedata.com/resource/pubmed/grant/R01 GM067173-08,
http://linkedlifedata.com/resource/pubmed/grant/R01 GM067173-09,
http://linkedlifedata.com/resource/pubmed/grant/R01 GM67163,
http://linkedlifedata.com/resource/pubmed/grant/RR08389-01
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Amides,
http://linkedlifedata.com/resource/pubmed/chemical/Aza Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Carbamates,
http://linkedlifedata.com/resource/pubmed/chemical/Ethers,
http://linkedlifedata.com/resource/pubmed/chemical/Ligands
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pubmed:status |
MEDLINE
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pubmed:month |
Oct
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pubmed:issn |
1520-5126
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
13
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pubmed:volume |
132
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
14027-9
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pubmed:dateRevised |
2011-10-13
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pubmed:meshHeading | |
pubmed:year |
2010
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pubmed:articleTitle |
Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.
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pubmed:affiliation |
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
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