A three-step tandem process for the synthesis of bicyclic gamma-lactams.
A one-pot, three-step tandem process has been developed for the direct synthesis of functionalised bicyclic [3.3.0], [4.3.0] and [5.3.0] gamma-lactams from simple allylic trichloroacetimidates. The process involves a palladium(ii) mediated Overman rearrangement followed by the use of Grubbs first generation complex which catalyzes both a ring closing metathesis reaction and a Kharasch cyclization. As well as exploring the scope of this process for the synthesis of a range of functionalised bicyclic gamma-lactams, the use of chiral palladium(ii) catalysts during the Overman rearrangement for the enantioselective synthesis of the bicyclic gamma-lactams is also demonstrated.
McGonagle
Fiona I
FI
WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UKG12 8QQ.
Brown
Lindsay
L
Cooke
Andrew
A
Sutherland
Andrew
A
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007769:Lactams; D010165:Palladium