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Novel Synthesis of 1,6,7,9-Tetrasubstituted 8-Oxo-1-azaspiro[4.4]nonanes


D Gravestock
JM McKenzie

Abstract

The synthesis and isolation of one diastereomer of 1-benzyl-7,9-dimethyl-8-oxo-1-azaspiro[4.4]nonane-6-carbonitrile 11 was accomplished by the diiron nonacarbonyl-assisted spirocyclization reaction of 2-(1-benzyl-2-pyrrolidinylidene)acetonitrile 10 and 2,4-dibromo-3-pentanone 12.NOESY NMR spectroscopy experiments of 11 showed it to be the (5R*, 6S*, 7S*, 9S*)-diastereomer.


South African Journal of Chemistry Vol.55 2002: 132-

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eISSN: 1996-840X
print ISSN: 0379-4350