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Diversity-oriented synthesis of azaspirocycles

Wipf, P and Stephenson, CRJ and Walczak, MAA (2004) Diversity-oriented synthesis of azaspirocycles. Organic Letters, 6 (17). 3009 - 3012. ISSN 1523-7060

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Abstract

(Equation Presented) 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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Stephenson, CRJ
Walczak, MAA
Date: 19 August 2004
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 6
Number: 17
Page Range: 3009 - 3012
DOI or Unique Handle: 10.1021/ol0487783
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Aza Compounds--chemical synthesis; Chemistry, Organic--methods; Cyclization; Indicators and Reagents; Molecular Structure; Spiro Compounds--chemical synthesis
PubMed ID: 15330670
Date Deposited: 30 Jan 2014 18:15
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/20420

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