Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones.
The cycloaddition of alkynylboronates and sydnones provides a convenient and highly regioselective method for the synthesis of a broad range of di-, tri-, and tetrasubstituted pyrazole boronic esters. The origins of an observed regiochemical divergence in the reactions of terminal alkynylboronates with their more substituted analogues have been studied by DFT methods.
Browne
Duncan L
DL
Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom.
Vivat
Jérôme F
JF
Plant
Andrew
A
Gomez-Bengoa
Enrique
E
Harrity
Joseph P A
JP
D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis; D003500:Cyclization; D008958:Models, Molecular; D011720:Pyrazoles / Q000138:chemical synthesis*
D000480:Alkynes; D001897:Boronic Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011720:Pyrazoles