Source:http://linkedlifedata.com/resource/pubmed/id/17346029
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
6
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pubmed:dateCreated |
2007-3-9
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pubmed:abstractText |
A highly efficient method for the synthesis of 1-azabicyclo[x.y.0]alkane amino acid derivatives and their congeners by means of extremely regioselective cyclohydrocarbonylation (CHC) is described. The CHC reactions are catalyzed by Rh-BIPHEPHOS complex under mild conditions. These CHC reaction processes involve (i) an extremely linear-selective hydroformylation of the terminal alkene moiety of a dehydrodipeptide substrate, (ii) intramolecular condensation to form cyclic N-acyliminium key intermediate, and (iii) the second cyclization through intramolecular nucleophilic addition of a heteoatom nucleophile to the cyclic N-acyliminium moiety to afford the corresponding 1-azabicyclo[x.y.0] system. This consecutive double cyclization process proceeds with extremely high diastereoselectivity in most cases. This method has been successfully applied to the syntheses of 1-azabicyclo[4.4.0], -[5.4.0], and -[4.3.0] systems. The mechanisms of the reactions and the rationale for the observed extremely high diastereoselectivity are presented. This Rh-catalyzed CHC process would serve as a highly efficient and versatile method for the syntheses of a variety of conformationally restrained dipeptides, peptidomimetics, alkaloids, and other biologically active natural or unnatural products.
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pubmed:grant | |
pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-11031021,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-12489933,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-15795926,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-2410151,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-8558518,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-8759637,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-9171867,
http://linkedlifedata.com/resource/pubmed/commentcorrection/17346029-9733491
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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/Alkanes,
http://linkedlifedata.com/resource/pubmed/chemical/Amino Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Bicyclo Compounds, Heterocyclic,
http://linkedlifedata.com/resource/pubmed/chemical/Hydrocarbons, Cyclic,
http://linkedlifedata.com/resource/pubmed/chemical/Rhodium
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0022-3263
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
16
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pubmed:volume |
72
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1871-82
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pubmed:dateRevised |
2011-9-26
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pubmed:meshHeading | |
pubmed:year |
2007
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pubmed:articleTitle |
Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation.
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pubmed:affiliation |
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, N.I.H., Extramural
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