Novel bicyclization reaction leading to a fused beta-lactone.
[reaction: see text] The reaction of acrylyl chloride with the above amino ketone in the presence of pyridine produces bicyclic beta-lactones rather than the corresponding acrylamide, which can be the major product under other conditions.
Reddy
Leleti Rajender
LR
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
D000178:Acrylamides / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
D000178:Acrylamides; D000577:Amides; D002712:Chlorides; D007783:Lactones; D011725:Pyridines