The synthesis of aza[n]ladderanes and azahomo[n]ladderanes containing β-lactams at the terminus
Date
1997
Authors
Warrener, R.N.
Russell, R.A.
Margetic, D.
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Synlett: accounts and rapid communications in synthetic organic chemistry, 1997; 1997(1):38-40
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Ronald N. Warrener, Richard A. Russell, Davor Margetic
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Abstract
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.
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© Georg Thieme Verlag