Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals.

Carbogallation of alkynes using gallium tribromide and silyl ketene acetals and synthetic application to cross-coupling with aryl iodides.

A domino pericyclic route to polysubstituted salicylic acid derivatives: four sequential processes from enynones and ketene silyl acetals.

Alkenyl alkynyl ketones and ketene silyl acetals (KSAs) undergo regioselective [2+2]-cycloaddition under thermal conditions, triggering domino pericyclic reactions en route to various poly-substituted salicylic acid derivatives.

Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor.

Based on a preactivation protocol with (p-Tol)2SO/Tf2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O-oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophili...

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.

The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis a...

One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst.

In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF₄) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of the desired γ-lactones were directly prepared with high regioselectivities and yields in a simpl...