Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives.
Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and alpha-bromoamide is also discussed.
Matsubara
Seijiro
S
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto, Japan. matsubar@mc.kyoto-u.ac.jp
Kasuga
Yuri
Y
Yasui
Takuya
T
Yoshioka
Masahito
M
Yamin
Bohari
B
Utimoto
Kiitiro
K
Oshima
Koichiro
K
D000215:Acylation; D001685:Biological Factors / Q000138:chemical synthesis; D008958:Models, Molecular; D008968:Molecular Conformation; D010075:Oxathiins / Q000737:chemistry*; D013237:Stereoisomerism
D001685:Biological Factors; D010075:Oxathiins