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:	Creators Email Pitt Username ORCID Wipf, P pwipf@pitt.edu PWIPF 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-dev.library.pitt.edu/id/eprint/20420

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