141081-81-4Relevant articles and documents
Asymmetric desymmetrization of prochiral 1,3-diols via diastereoselective C-O bond fission of bicyclic acetal using a chiral sulfoxide as a chiral auxiliary
Maezaki, Naoyoshi,Murakami, Manabu,Soejima, Motohiro,Tanaka, Tetsuaki,Imanishi, Takeshi,Iwata, Chuzo
, p. 1146 - 1151 (2007/10/03)
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.