Intramolecular ene reaction of a chiral bicyclic lactam.
The preparation of bicylic lactam 2 is described, employing an acetoacetate-based synthesis of 1,4-ketoacid 3. The lactam 2 was shown to undergo a thermal ene reaction at 280-300 degrees C to afford tricycle 7. Reduction of the ene product followed by removal of the chiral auxiliary fragment provided the unusual lactam system 9 in highly enantioenriched form.
Resek
James E
JE
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80503, USA. resek_j@ricerca.com
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D007769:Lactams / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007769:Lactams