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Wipf, P. et al.

Wipf, Stephenson, Walczak,

Diversity-oriented synthesis of azaspirocycles.

Multicomponent condensation of N-diphenylphosphinoylimines, alkynes, zirconocene hydrochloride, and diiodomethane provides a rapid access to omega-unsaturated dicyclopropylmethylamines. These novel building blocks are converted into heterocyclic 5-azaspiro[2.4]heptanes, 5-azaspiro-[2.5]octanes, and 5-azaspiro[2.6]nonanes by means of selective ring-closing metathesis, epoxide opening, or reductive amination. The resulting functionalized pyrrolidines, piperidines, and azepines are scaffolds of considerable relevance for chemistry-driven drug discovery.[1]

References

Diversity-oriented synthesis of azaspirocycles. Wipf, P., Stephenson, C.R., Walczak, M.A. Org. Lett. (2004) [Pubmed]

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