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A direct synthesis of α-(hydroxymethyl) and α-alkyl-vinyl alkyl ketones

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
47
Issue
39
Identifiers
DOI: 10.1016/j.tetlet.2006.07.093
Keywords
  • Baylis–Hillman
  • α-Hydroxmethyl Alkyl Vinyl Ketones
  • α
  • β-Unsaturated Alkyl Ketones

Abstract

Abstract Reaction of 2,4-diketoesters 3a– c with aqueous formaldehyde using potassium carbonate solution as base affords the corresponding α-methylene-β-hydroxyalkanones 4a– c which provide a route to α,β-unsaturated alkyl ketones 6a– e via coupling of α-acetoxymethyl alkyl vinyl ketone 5a with Grignard reagents in the presence of a catalytic amount of LiCuBr 2 at low temperature.

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