Lanthanide-catalyzed endo- and enantioselective 1,3-dipolar cycloaddition reactions of nitrones with alkenes
✍ Scribed by Ana I. Sanchez-Blanco; Kurt V. Gothelf; Karl Anker Jørgensen
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 232 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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## 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
## Abstract 1,3‐Dipolar cycloaddition of nitrones with ethyl vinyl ether or 2,3‐dihydrofuran proceeds smoothly in the presence of a catalytic amount (10 mol%) of ytterbium triflate to afford isoxazolidines and dicyclic isoxazolidine respectively with good yields and high stereoselectivity.