Silicon-Directed Rhenium-Catalyzed Allylic Carbaminations and Oxidative Fragmentations of [gamma]-Silyl Allylic Alcohols

A highly regioselective allylic substitution of [beta]-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 al...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-04, Vol.20 (17), p.4891-4895
Main Authors: Chavhan, Sanjay W, Cook, Matthew J
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Amines
Chemistry
Fragmentation
High temperature
Joining
Level (quantity)
Pathways
Silanes
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Summary:A highly regioselective allylic substitution of [beta]-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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201400104