Abstract
A practical and high yielding synthetic route was developed for the preparation of optically pure (R)-(+)-2-bis(pentafluorophenyl)boryl-, (R)-(+)-1a,b, and (R)-2-difluoroboryl-1,1′-binaphthyls, (R)-5a,b. Chiral boranes (R)-1a and (R)-5a are active catalysts for the allylstannation of aromatic aldehydes although enantioselectivities for R products were low. A structural investigation of the adduct (±)-1a·o-anisaldehyde suggested that substituents in the 2′-position of the binaphthyl backbone could increase enantiofacial discrimination. Consistent with this structural study, the 2′-Me derivative (R)-1b gave slightly higher enantioselectivities and opposite configuration S of homoallylic alcohol products.
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