Unprecedented double benzylic rearrangement: regio- and stereospecific tandem 1,4-shift and Curtin rearrangement
Tetrahedron, ISSN: 0040-4020, Vol: 68, Issue: 39, Page: 8276-8285
2012
- 7Citations
- 3Captures
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Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
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Article Description
An α-benzyloxyketone forming part of a strained cyclopentane carbon framework when treated with 10 equiv of anhydrous NaOH in absolute ethanol, for 2 h, affords in a 65% yield a new 2-benzyl-2-hydroxyketone, resulting from an unprecedented double benzylic rearrangement. This new rearrangement could be interpreted as an initial benzylic 1,4-shift between the O -enolate alkoxide of the ketone group and the oxygen atom of the benzyloxy ether, followed by a Curtin type benzylic 1,2-shift. Apart from the novelty and the synthetic application of this transformation it is worth noting the complete regio- and stereoselectivity observed. The structures of both substrate and product have been confirmed by X-ray diffraction studies. A tentative mechanism is herein proposed.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040402012011246; http://dx.doi.org/10.1016/j.tet.2012.07.053; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84865067340&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040402012011246; https://dx.doi.org/10.1016/j.tet.2012.07.053
Elsevier BV
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