George P. Luke

An Efficient Preparation of β-Aryl-β-ketophosphonates by the TFAA/ H3PO4-Mediated Acylation of Arenes with Phosphonoacetic Acids

Beta-aryl-beta-ketophosphonates can be efficiently prepared in good yield by using a TFAA/85% H 3PO 4-mediated acylation of electron-rich arenes with phosphonoacetic acids. The conditions offer advantages over existing methods of preparing these useful compounds by not requiring the use of strong base, cryogenics, or an anhydrous and inert atmosphere. Furthermore, some functional groups not tolerated with the reaction conditions used in existing methods are compatible with the herein described conditions.

A titanium (IV) mediated one-pot double condensation synthesis of 5,6-dihydro-4H-pyran-4-ones

Abstract An alternative method for the synthesis of 2-amino-5,6-dihydro-4H-pyran-4-ones and 5,6-dihydro-4H-pyran-4-ones is described. This preparation makes use of the condensation of titanium enolates derived from β-hydroxy ketones with phosgene iminium chloride or trimethylorthoformate, respectively. The in situ formation of the necessary titanium complex from an aldol condensation using simple ketone and aldehyde precursors makes for a one-pot double condensation synthesis of the desired dihydropyrones.