An efficient reaction cascade delivering a series of pyrrolo[1,2-a]quinolines bearing phosphonate or phosphine oxide moieties is presented. This sequence exploits the in situ transformation of propargylic alcohols into transient allenes by means of a strategic [2,3]-sigmatropic rearrangement followed by trapping of the resulting allenes by an adjacent pyrrole ring. Furthermore, the initial smal...

We have previously clarified that the strongly electron-withdrawing CF3 group nicely affected base-mediated proton shift of CF3-containing propargylic or allylic alcohols to afford corresponding α,β-unsaturated saturated ketones, respectively, which was applied this time Claisen rearrangement after O-allylation with a group, followed by isomerization allyl vinyl ethers via shift, enabling desir...

The stereoselective germylzincation of internal alkynes delivering trisubstituted vinylgermanes is achieved via a radical chain process involving Ph3GeH and Et2Zn with AIBN as initiator. Excellent levels regiocontrol are observed for non-symmetric (aryl, alkyl)-substituted alkynes, well propargylic alcohols aryl-, alkyl-, or silyl-substituted alkynes. reaction can be combined in one pot the Cu(...

[reaction: see text] The reactions of propargylic alcohols, aliphatic primary amines, and CO2 were conducted in CuCl/[BMIm]BF4 system to produce the corresponding 5-methylene-1,3-oxazolidin-2-ones under relatively mild conditions. The products could be conveniently isolated by means of liquid-liquid extraction. The solvent ionic liquid as well as CuCl catalyst can be recovered and reused three ...

Ephedrine-derived sulfamide-amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O(i)Pr)4 and Zn(OTf)2. It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N-methylephedrine under the same reaction cond...

The extremely mild and highly efficient catalytic generation of non-metalated, conjugated acetylides is reported. These acetylides are used to generate enol-protected functionalized propargylic alcohols 1, 1,3-dioxolane compounds 2, or 3,4,5-trisubstituted 4,5-dihydrofurans 4 through serial multibond-forming processes. The method calls for a nucleophile (a tertiary amine or phosphine) as a chem...

With the aim of profitable conversion carbon dioxide (CO2) in an efficient, economical, and sustainable manner, we developed a CuBr/ionic liquid (1-butyl-3-methylimidazolium acetate) catalytic system that could efficiently catalyze three-component reactions propargylic alcohols, 2-aminoethanols, CO2 to produce 2-oxazolidinones ?-hydroxy ketones. Remarkably, this employed lower metal loading (0....