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Silicon‐Directed Rhenium‐Catalyzed Allylic Carbaminations and Oxidative Fragmentations of γ‐Silyl Allylic Alcohols
Authors:Dr Sanjay W Chavhan  Dr Matthew J Cook
Institution:School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast. BT9 5AG (Northern Ireland), Fax: (+44)?28‐9097‐6524
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.
Keywords:allylic substitution  carbamination  Hiyama coupling  rhenium  silicon
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