Diastereoselective formation of β-hydroxyketones by the reduction of Ketene dimers

PH Wei, MA Gary, D Nalla, GD Harzmann, AA Ibrahim…

Index: Wei, Pei-Hsun; Gary, Melanie A.; Nalla, Divya; Harzmann, Gero D.; Ibrahim, Ahmad A.; Dayak, Kyle R.; Kerrigan, Nessan J. Tetrahedron Letters, 2013 , vol. 54, # 8 p. 932 - 935

Full Text: HTML

Citation Number: 1

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, ...