✍ Scribed by David A Nugiel
No coin nor oath required. For personal study only.
Substituted indenones reacted smoothly with a variety of in situ generated nitrones in the presence of lanthanide triflates to give exclusive exo 1,3-dipolar cycloaddition products in high yield. Judicious choice of the nitrone substituents allowed for further modification of the indenoisoxazolidine core to the corresponding indenoisoxazoline and indenoisoxazole analogs in high yield.
📜 SIMILAR VOLUMES
Phenyl aziridines undergo 1,3-dipolar cycloaddition efficiently with olefins such as cyclic enol ethers and allyltrimethylsilane in the presence of a catalytic amount of Sc(OTf) 3 at ambient temperature to afford the corresponding pyrrolidine derivatives in high yields with high regioselectivity.
## Abstract magnified image Regio‐ and stereoselective 1,3‐dipolar cycloaddition of nitrile oxides to internal 2‐pentenols, α,β‐unsaturated esters and amides catalyzed by __R__‐(+) BINOL‐lanthanide complexes affords corresponding 3‐aryl‐2‐isoxazolines with enantioselectivities up to 89% ee.
1,3-Dipolar cycloaddition reactions of polymer-supported nitrones with alkenes proceeded smoothly in the presence of a catalytic amount of a lanthanide triflate to afford the corresponding 2-isoxazolines in high yields. Diverse 2-isoxazoline derivatives were prepared based on these solid-phase react