Chemical and Pharmaceutical Bulletin p. 1146 - 1151 (1996)
Update date:2022-09-26
Topics:
Maezaki, Naoyoshi
Murakami, Manabu
Soejima, Motohiro
Tanaka, Tetsuaki
Imanishi, Takeshi
Iwata, Chuzo
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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