281667-70-7Relevant articles and documents
C2-symmetric bis-sulfoxide: A novel chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols
Maezaki, Naoyoshi,Sakamoto, Atsunobu,Nagahashi, Noboru,Soejima, Motohiro,Li, Ying-Xia,Imamura, Tsuneaki,Kojima, Naoto,Ohishi, Hirofumi,Sakaguchi, Ken-Ichi,Iwata, Chuzo,Tanaka, Tetsuaki
, p. 3284 - 3291 (2000)
A new heterocyclic compound, C2-symmetric bis-sulfoxide 1, has been found to be an efficient chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols via diastereoselective acetal fission. Both (R,R)- and (S,S)-1 are readily synthesized with high optical purity via asymmetric oxidation of 1,5-benzodithiepan-3-one (2). After acetalization of meso-1,2- diols 6a-e and a mono-TMS ether 6f with this chiral auxiliary 1, the resulting acetals 7a-f were subjected to base-promoted acetal fission upon treatment with potassium hexamethyldisilazide (KHMDS) followed by acetylation or benzylation to give the desymmetrized diol derivatives 8a-f with high diastereoselectivity. The chiral auxiliary 1 is readily removed by acid- promoted hydrolysis and can be recovered without a loss in enantiomeric excess.