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

Naoyoshi MAEZAKI; Manabu MURAKAMI; Motohiro SOEJIMA; Tetsuaki TANAKA; Takeshi IMANISHI; Chuzo IWATA

doi:10.1248/cpb.44.1146

Naoyoshi MAEZAKI, Manabu MURAKAMI, Motohiro SOEJIMA, Tetsuaki TANAKA, Takeshi IMANISHI, Chuzo IWATA

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Keywords: asymmetric desymmetrization, prochiral 1, 3-diol, sulfinyl chirally, α-sulfinyl acetal, β-elimination

JOURNAL FREE ACCESS

1996 Volume 44 Issue 6 Pages 1146-1151

DOI https://doi.org/10.1248/cpb.44.1146

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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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