Oxygen-directed intramolecular hydroboration.
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.
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Robert-André F
RA
Rarig
Matthew
M
Scheideman
Edwin
E
Vedejs
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D010084:Oxidation-Reduction; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry
D000438:Alcohols; D000475:Alkenes; D001880:Boranes; D020005:Propanols; C006463:allyl alcohol; D007455:Iodine