10.1021/ol800921n.s001
Stephen P. Marsden
Stephen P.
Marsden
Alison E. McGonagle
Alison E.
McGonagle
Ben McKeever-Abbas
Ben
McKeever-Abbas
Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis
American Chemical Society
2008
iminophosphorane
Catalytic
organophosphorus component
Cyclization
involvement
benzoxazole
azole
reaction efficiency
cyclization
azine
heterocycle synthesis
formation
mol
phenanthridine
phosphine oxide
Heteroaromatic Synthesis
spectroscopy
catalyst loadings
2008-06-19 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Catalytic_aza_Wittig_Cyclizations_for_Heteroaromatic_Synthesis/2933194
The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.