Stereospecific alpha-methallylation of hydroxyaldehydes by silatropic ene cyclisation
We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)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 consti...
| Main Authors: | , , |
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| Format: | Journal article |
| Sprog: | English |
| Udgivet: |
2009
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| Summary: | We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)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. © 2009 Elsevier Ltd. All rights reserved. |
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