A novel, high-yielding approach to a chiral inducer: (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol

A new method for preparing (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol in high yield based on selective 2,3-spiroboration of (2R,3R)-1,1,4,4-tetraphenylbutanetetraol has been developed. It avoids traditional oxidation and reduction steps, and provides a simplified, more straightforward, and high-yielding synthesis of the title compound.

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Potassium (2R,3R,7R,8R)-2,3,7,8-tetrakis(hydroxydiphenylmethyl)-1,4,6,9-tetraoxa-5-boraspiro[4.4]nonan-5-uideC56H48BKO8[α]D25=+169.7 (c 0.13, MeOH)Source of chirality: the precursorAbsolute configuration: (2R,3R,7R,8R)

Sodium (2R,3R,7R,8R)-2,3,7,8-tetrakis(methoxydiphenylmethyl)-1,4,6,9-tetraoxa-5-boraspiro[4.4]nonan-5-uideC60H56BNaO8[α]D25=+16.7 (c 0.8, DMSO)Source of chirality: the precursorAbsolute configuration: (2R,3R,7R,8R)

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diolC30H30O4[α]D15=+59.6 (c 0.08, CDCl3)Source of chirality: the precursorAbsolute configuration: (2R,3R)