Diversity-oriented synthesis of azaspirocycles

Organic Letters
Peter WipfMaciej A A Walczak

Abstract

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.

References

Jul 18, 2001·Journal of the American Chemical Society·P WipfC R Stephenson
Aug 17, 2001·Organic Letters·P Wipf, C Kendall
Apr 5, 2002·Chemistry : a European Journal·Peter Wipf, Christopher Kendall
May 31, 2002·Journal of Medicinal Chemistry·Daniel F VeberKenneth D Kopple
Jul 5, 2003·Organic Letters·Peter Wipf, Corey R J Stephenson
Jun 17, 2004·Journal of the American Chemical Society·Soon Hyeok HongRobert H Grubbs

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Citations

Feb 12, 2011·ACS Combinatorial Science·Erik FensterPaul R Hanson
May 9, 2008·Journal of the American Chemical Society·Maciej A A Walczak, Peter Wipf
Mar 30, 2006·Proceedings of the National Academy of Sciences of the United States of America·Rudi BereraJohn T M Kennis
Jun 9, 2005·Current Opinion in Chemical Biology·Suzanne FergusDavid R Spring
Jun 9, 2005·Current Opinion in Chemical Biology·Shiying Shang, Derek S Tan
Dec 14, 2006·Organic & Biomolecular Chemistry·David L WallerPeter Wipf
May 20, 2006·Angewandte Chemie·Peter Wipf, Maciej A A Walczak
Mar 19, 2013·Chemical Communications : Chem Comm·Rodney A Fernandes, Vijay P Chavan
Sep 25, 2004·Organic Letters·Peter WipfTyler E Benedum
Mar 22, 2012·Organic Letters·Zhengxin CaiMichael Harmata
Jun 15, 2006·Chemical Reviews·Daniel P Walsh, Young-Tae Chang

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