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Org Lett. 2010 Jan 15;12(2):336-9. doi: 10.1021/ol902681t.

Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes.

Author information

1
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.

Abstract

Enantioenriched allenylsilanes are used in three-component propargylation reactions with aldehydes and silyl ethers to form syn-homopropargylic ethers that contain an imbedded azide. These materials then undergo thermally induced intramolecular 1,3-dipolar cycloaddition reactions, resulting in unique fused ring systems containing 1,2,3-triazoles. The ability to modify all three components of the reaction allows for expedient access to compounds containing significant structural and stereochemical variation.

PMID:
20017521
PMCID:
PMC3164318
DOI:
10.1021/ol902681t
[Indexed for MEDLINE]
Free PMC Article

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