P-C bond formation in reactions of Morita-Baylis-Hillman adducts with phosphorus nucleophiles

Abstract

Morita-Baylis-Hillman adducts (e.g., activated allyl acetates or bromides) are an unprecedented trifunctional synthetic platform for diverse types of nucleophilic displacements, additions and rearrangements. These reactions can proceed in an inter-or intramolecular manner, and with stereoselective induction. Accordingly, they contribute, as the key steps, to numerous synthetic pathways, including the total syntheses of natural products of various classes and to novel strategies leading to medicinally relevant compounds and commercialized drugs. The synthetic feasibility of the Morita-Baylis-Hillman adducts in organophosphorus chemistry has been explored to a relatively low extent. In this review, we summarize the current state of the art on the formation of the C-P bond by means of the title reactions. The scope of the processes, the stereochemistry of the products and their further synthetic relevance to obtain multifunctional compounds, including those that are biologically active, are summarized.

Copper-Catalyzed Oxidative sp3-Carbon Radical Cross-Coupling with Trialkylphosphites Leading to α-Phosphonyl 1,3-Dicarbonyl Compounds

“…The construction of carbon–phosphorus bonds has become a topic of immense interest due to their importance as versatile intermediates in chemical synthesis . In recent years, significant efforts have been made toward the development of methods for the making of this kind of bond.…”