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Synlett 1997; 1997(1): 38-40
DOI: 10.1055/s-1997-697
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The Synthesis of Aza[n]ladderanes and Azahomo[n]ladderanes Containing β-Lactams at the Terminus

Ronald N. Warrener* , Richard A. Russell, Davor Margetic
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia, Fax +61 79 30 9917; internet r.warrener@cqu.edu.au
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Publication Date:
22 March 2004 (online)

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5-Azabicyclo[2.2.0]hex-2-en-6-one 1 undergoes [2π+2π] cycloaddition with dimethyl acetylene dicarboxylate (Ru-catalysed) to yield aza[3]ladderane 2 which is transformed to aza[5]ladderanes 4 and 5 on treatment with cyclobutadiene and to azahomo[5]ladderanes 10 and 11 on reaction with cyclopentadiene. The specifities of these cycloaddition reactions are in agreement with predictions made using ab initio calculations. Chlorosulfonylisocyanate addition is used to access azahomo[4]ladderane 14.

cycloaddition-specifities - polycyclobutanes - chlorosulfonyl isocyanate - ab initio calculations - 5-azabicyclo[2.2.0]hex-2-en-6-one