New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
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.
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
Sébastien
S
Comesse
Morgane
M
Sanselme
Adam
A
Daïch
D001372:Aza Compounds / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001372:Aza Compounds; D007769:Lactams; D011758:Pyrroles; D011804:Quinolines; C410408:martinelline