Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 3503-3508 |
| Number of pages | 6 |
| Journal | Tetrahedron Letters |
| Volume | 50 |
| Issue number | 26 |
| Early online date | 18 Mar 2009 |
| DOIs | |
| Publication status | Published - 1 Jul 2009 |
Bibliographical note
M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.CAPLUS AN 2009:603551(Journal)
Keywords
- decarboxylative Claisen rearrangement furanylethyl tosylacetate
- ethylidenetosylmethyldihydrofuran prepn stereoselective reaction electrophile
- furan ethylidenetosylmethyldihydro prepn stereoselective reaction electrophile
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