Open AccessOxygen-Directed Intramolecular Hydroboration
Author(s) -
Robert-André F. Rarig,
Matthew Scheideman,
Edwin Vedējs
Publication year - 2008
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja800402g
Subject(s) - chemistry , hydroboration , regioselectivity , intramolecular force , oxygen , organoboron compounds , branching (polymer chemistry) , stereochemistry , organic chemistry , boron , catalysis
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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