Asymmetric Desymmetrization of Prochiral 1,3-Diols via Diastereoselective C-O Bond Fission of Bicyclic Acetal Using a Chiral Sulfoxide as a Chiral Auxiliary.

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Abstract
Asymmetric desymmetrization of a prochiral 1, 3-diol was established by diastereoselective C-O bond fission of the chiral α-sulfinyl acetal 6. Treatment of 6 with titanium tetrachloride afforded mainly 7a via an oxonium intermediate, while with lithium diisopropylamide 7b was selectively obtained via diastereoselective β-elimination followed by an olefin isomerization.

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