New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Identifieur interne : 000D48 ( Main/Exploration ); précédent : 000D47; suivant : 000D49New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Auteurs : Sébastien Comesse [France] ; 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
Affiliations:
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Le document en format XML
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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></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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