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Oxygen-directed intramolecular hydroboration.

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.

SUBMITTER: Rarig RA

PROVIDER: S-EPMC2646882 | biostudies-other | 2008 Jul

REPOSITORIES: biostudies-other

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Oxygen-directed intramolecular hydroboration.

Rarig Robert-André F RA Scheideman Matthew M Vedejs Edwin E

Journal of the American Chemical Society 20080624 29

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. ...[more]

PMID: 18572941

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