The decarboxylative Claisen rearrangement (dCr) reaction of 1-(furan-2-yl)ethyl 2-tosylacetate afforded 2-ethylidene-3-(tosylmethyl)-2,3-dihydrofuran. Reaction of the dearomatized heterocycle with a variety of electrophiles gave addn. products with excellent syn-diastereoselectivity. The furanol adducts were then utilized as functionalized scaffolds for a series of subsequent transformations.
- decarboxylative Claisen rearrangement furanylethyl tosylacetate
- ethylidenetosylmethyldihydrofuran prepn stereoselective reaction electrophile
- furan ethylidenetosylmethyldihydro prepn stereoselective reaction electrophile
Camp, J. E., & Craig, D. (2009). Reactivity of dearomatised furans synthesized via the decarboxylative Claisen rearrangement. Tetrahedron Letters, 50(26), 3503-3508. https://doi.org/10.1016/j.tetlet.2009.03.091