Asymmetric desymmetrization of prochiral 1,3-diols via diastereoselective C-O bond fission of bicyclic acetal using a chiral sulfoxide as a chiral auxiliary

DOI: 10.1248/cpb.44.1146

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1146 - 1151 (1996)

Update date:2022-09-26

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Authors:

Maezaki, Naoyoshi

Murakami, Manabu

Soejima, Motohiro

Tanaka, Tetsuaki

Imanishi, Takeshi

Iwata, Chuzo

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Article abstract of DOI:10.1248/cpb.44.1146

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.

Full text of DOI:10.1248/cpb.44.1146

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