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Letter

Diversity-Oriented Synthesis of Azaspirocycles

Supporting Info

Peter Wipf,* Corey R. J. Stephenson, and Maciej A. A. Walczak

Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

Org. Lett., 2004, 6 (17), pp 3009–3012

DOI: 10.1021/ol0487783

Publication Date (Web): July 28, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pwipf@pitt.edu

Abstract

Multicomponent condensation of N-diphenylphosphinoylimines, alkynes, zirconocene hydrochloride, and diiodomethane provides a rapid access to ω-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.

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Published In Issue August 19, 2004
Received June 26, 2004

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Letter

Diversity-Oriented Synthesis of Azaspirocycles

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Chemoselectivity: The Mother of Invention in Total Synthesis

Can Two Molecules Have the Same NMR Spectrum? Hexacyclinol Revisited

Enantioselective Intramolecular Friedel−Crafts-Type α-Arylation of Aldehydes

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