Title of article :
Diastereoselective formation of β-hydroxyketones by the reduction of Ketene dimers
Author/Authors :
Wei، نويسنده , , Pei-Hsun and Gary، نويسنده , , Melanie A. and Nalla، نويسنده , , Divya and Harzmann، نويسنده , , Gero D. and Ibrahim، نويسنده , , Ahmad A. and Dayak، نويسنده , , Kyle R. and Kerrigan، نويسنده , , Nessan J.، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2013
Abstract :
A general method for the diastereoselective formation of β-hydroxyketones by the reduction of ketene dimers was developed. The reduction of ketene homodimers, derived from alkylarylketenes and dimethylketene, and ketene heterodimers, derived from methylketene and ethylphenylketene or diphenylketene, was investigated. Methylphenylketene dimer was reduced with optimal diastereoselectivity (dr = 6:1) using LiBH4. However, more generally, LiAlH4 was found to be the most effective reducing system with respect to diastereoselectivity (dr up to >99:1) and yield (62–>99% for 10 examples).
Keywords :
Ketene heterodimer , ?-Lactones , Reduction , diastereoselective , ?-Hydroxyketones , Enolates , Enantioenriched , Disubstituted ketenes , Ketoketenes , Ketene dimer , Chiral
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters
