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. 2008 Jul 23;130(29):9182-3.
doi: 10.1021/ja800402g. Epub 2008 Jun 24.

Oxygen-directed intramolecular hydroboration

Robert-André F Rarig  1 , Matthew Scheideman, Edwin Vedejs
Affiliations

Oxygen-directed intramolecular hydroboration

Robert-André F Rarig et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

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