Stereospecific α-(methyl)allylation of hydroxyaldehydes by silatropic ene cyclisation
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- Dr Michael Hall
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| Author(s) | | Robertson J, Hall MJ, Green SP |
| Publication type | | Article |
| Journal | | Tetrahedron |
| Year | | 2009 |
| Volume | | 65 |
| Issue | | 28 |
| Pages | | 5541-5551 |
| ISSN (print) | | 0040-4020 |
| ISSN (electronic) | | 1464-5416 |
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| Full text for this publication is not currently held within this repository. Alternative links are provided below where available. |
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| We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotyl-silyl)oxy substituent. The transformations are best described mechanistically as intramolecular silatropic ene reactions based on stereoselectivity, kinetic, and computed transition state data. The overall process constitutes a stereospecific (meth)allylation of α-hydroxyaldehydes, under neutral conditions, in which the hydroxyl protecting group is also the (meth)allylating agent. |
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| Publisher | | Pergamon |
| URL | | http://dx.doi.org/10.1016/j.tet.2009.01.117 |
| DOI | | 10.1016/j.tet.2009.01.117 |
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