Highly functionalised monocyclic and bicyclic β-lactams via alkene metathesis

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Anthony G. M. Barrett, Simon P. D. Baugh, Vernon C. Gibson, Matthew R. Giles, Edward L. Marshall and Panayiotis A. Procopiou


Abstract

Both monocyclic and bicyclic β-lactam systems are prepared via alkene metathesis reactions using Mo([double bond, length as m-dash]CHCPhMe2)- ([double bond, length as m-dash]NC6H3Pri2)[(OCMe(CF 3)2]2 or Ru([double bond, length as m-dash]CHPh)Cl2(PCy3)2.


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