An unexpected oxidation in the generation of cyclopenta[c]piperidines by ring-closing metathesis.
Ring-closing metathesis reaction of dienes A (n = 1, R = CO(2)R') leads to fused cyclopentenones C instead of the expected cyclopentene derivatives B. RCM reaction of the other dienes A takes place satisfactorily, affording the expected fused cycloalkene derivatives B. Cyclohexene B (n = 2, R = CO(2)R') also undergoes oxidation to the corresponding cyclohexenone C.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine, University of Barcelona, 08028 Barcelona, Spain. amat@ub.edu
Brunaccini
Elisa
E
Checa
Begoña
B
Pérez
Maria
M
Llor
Núria
N
Bosch
Joan
J
D003500:Cyclization; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010880:Piperidines