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Chemistry. 2014 Apr 22;20(17):4891-5. doi: 10.1002/chem.201400104. Epub 2014 Mar 27.

Silicon-directed rhenium-catalyzed allylic carbaminations and oxidative fragmentations of γ-silyl allylic alcohols.

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1
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:

Hiyama coupling; allylic substitution; carbamination; rhenium; silicon

PMID:
24677380
DOI:
10.1002/chem.201400104
[Indexed for MEDLINE]
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