A Strategy for the β‐selective conjugate addition of α‐fluoro‐β‐ketoamides to allenic esters has been developed via phosphine catalysis. This protocol exhibits a broad substrate scope, and a wide range of compounds bearing fluorinated quaternary carbon center was obtained in good to excellent yields. This protocol allows the use of γ‐substituted allenic esters to furnish the products with exclusive β‐selectivity.
Divergence in the PBu3-catalyzed [3+2] annulation of phenacylmalononitriles with allenoates, controlled by the γ-substitution on allenoates, offers a tunable synthesis of multifunctionalized cyclopentene carboxamides and cyclopentenols. An unprecedented formation of...
A 1,6-conjugate addition reaction of the Seyferth-Gilbert reagent (SGR) to p-quinone methides is reported. This base-mediated protocol allows rapid access to diarylmethylated diazomethylphosphonates. The reaction proceeds under mild basic conditions, making it a practical approach for the synthesis of diarylmethylated diazomethylphosphonates with a broad substrate scope. Interestingly, the treatment of the conjugate adduct with a catalytic amount of rhodium acetate resulted in the 1,2-aryl migration of the rhodium carbenoid intermediate to generate the corresponding 1,2-diaryl alkenylphosphonates in excellent yields.
An unexpected product-selectivity in the reaction of 2-arylideneindane-1,3-dione with dimethyl diazomethylphosphonate leading to the formation of two different types of products is reported. The reaction carried out in acetone in the presence of catalytic amount of cesium fluoride afforded spiropyrazoline phosphonates via 1,3-dipolar cycloaddition reaction, whereas the reaction in methanol yielded an interesting class of pyrazolylphthalides. This strategy provides an efficient alternative method for the construction of pyrazolylphthalides, and moreover, the process is general, works under mild conditions, and exhibits high functional group compatibility.
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