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Oxygen-directed intramolecular hydroboration

Rarig, RAF
; 
Scheideman, M
; 
Vedejs, E
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Genre
Journal Article
Date
2008-07-23
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Department
Subject
Alcohols
 Alkenes
 Boranes
 Iodine
 Oxidation-Reduction
 Propanols
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http://hdl.handle.net/20.500.12613/6084
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Oxygen-directed intramolecular hydroboration.pdf
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DOI
10.1021/ja800402g
Abstract
Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S·BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity. Copyright © 2008 American Chemical Society.
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American Chemical Society (ACS)
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Journal of the American Chemical Society
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