New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Identifieur interne : 000255 ( PubMed/Corpus ); précédent : 000254; suivant : 000256New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Auteurs : Sébastien Comesse ; Morgane Sanselme ; Adam DaïchSource :
- The Journal of organic chemistry [ 1520-6904 ] ; 2008.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Pyrroles, Quinolines.
- chemical , chemistry : Aza Compounds, Lactams, Pyrroles, Quinolines.
- Molecular Structure, Stereoisomerism.
Abstract
A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of (+/-)-martinelline alkaloids is also described.
DOI: 10.1021/jo702752w
PubMed: 18549283
Links to Exploration step
pubmed:18549283Le document en format XML
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<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<affiliation><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France. sebastien.comesse@univ-lehavre.fr</nlm:affiliation>
</affiliation>
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<author><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name>
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<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
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<affiliation><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France. sebastien.comesse@univ-lehavre.fr</nlm:affiliation>
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<author><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name>
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<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
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<series><title level="j">The Journal of organic chemistry</title>
<idno type="eISSN">1520-6904</idno>
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<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Stereoisomerism</term>
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<term>Quinolines</term>
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<term>Lactams</term>
<term>Pyrroles</term>
<term>Quinolines</term>
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<keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term>
<term>Stereoisomerism</term>
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<front><div type="abstract" xml:lang="en">A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of (+/-)-martinelline alkaloids is also described.</div>
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<Title>The Journal of organic chemistry</Title>
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<ArticleTitle>New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.</ArticleTitle>
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<Abstract><AbstractText>A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of (+/-)-martinelline alkaloids is also described.</AbstractText>
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