Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes.
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.
Brawn
Ryan A
RA
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.
Welzel
Morgan
M
Lowe
Jason T
JT
Panek
James S
JS
D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D000480:Alkynes; D001386:Azides; D004987:Ethers