Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 19.1 Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones at the ‘fork head’

Abstract

Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones was achieved by asymmetric deprotonation at the ‘fork head’ ketone system with Koga’s chiral base and subsequent ozonolysis of the resulting chiral silyl enol ether to give the cis-α,α′-disubstituted piperidine, pyrrolidine and hexahydroazepine, respectively, in high enantiomeric excess.

References

1. The previous paper entitled ‘Tandem Beckmann and Huisgen-White rearrangement as an alternative to the Bayer–Villiger oxidation of the bicyclo[3.3.1]nonane system: First asymmetric synthesis of (–)-dihydropalustramic acid. X-Ray molecular structure of 2β-ethyl-9-phenylsulfonyl-9-azabicyclo[3.3.1]nonan-3-one’[O. Muraoka, B.-Z. Zheng, K. Okumura, G. Tanabe, T. Momose and C. H. Eugster, J. Chem. Soc., Perkin Trans. 1, 1996, 1567] constitutes Part 18 of this seriesPart 17, T. Momose, K. Masuda, S. Furusawa, O. Muraoka and T. Itooka, Chem. Pharm. Bull., 1990, 38, 1707.
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