Silicon‐Directed Rhenium‐Catalyzed Allylic Carbaminations and Oxidative Fragmentations of γ‐Silyl Allylic Alcohols |
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Authors: | Dr Sanjay W Chavhan Dr Matthew J Cook |
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Institution: | School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast. BT9 5AG (Northern Ireland), Fax: (+44)?28‐9097‐6524 |
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Abstract: | A highly regioselective allylic substitution of β‐silyl allylic alcohols has been achieved that provides the branched isomer as a single product. This high level of regiocontrol is achieved through the use of a vinyl silane group that can perform a Hiyama coupling providing 1,3‐disubstituted allylic amines. An unusual oxidative fragmentation product was also observed at elevated temperature that appears to proceed by a Fleming–Tamao‐type oxidation–elimination pathway. |
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Keywords: | allylic substitution carbamination Hiyama coupling rhenium silicon |
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