A convenient synthesis of β,γ-unsaturated ketones via allylation of Z-1-halo-1-alkenyl-1,3,2-dioxaborolane

A convenient, general synthesis of β,γ-unsaturated ketones via allylation of Z-1-halo-1-alkenyl-1,3,2-dioxaborolane has been developed. The reactivity under different conditions and the effect of an additive, HMPA, is elucidated. A representative procedure for the synthesis of 1-nonen-3-one is descr...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 38; pp. 6963 - 6966
Main Authors Brown, Herbert C., Soundararajan, Raman
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.09.1994
Elsevier
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
FRIEDEL-CRAFTS ACYLATION
REARRANGEMENT
ALKENES
ACIDS
ESTERS
LITHIUM
DERIVATIVES
ORGANOBORANES
Organic boronate
Nucleophilic substitution
Aliphatic compound
Medium effect
Ketone
Allylation
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Summary:A convenient, general synthesis of β,γ-unsaturated ketones via allylation of Z-1-halo-1-alkenyl-1,3,2-dioxaborolane has been developed. The reactivity under different conditions and the effect of an additive, HMPA, is elucidated. A representative procedure for the synthesis of 1-nonen-3-one is described. Allylation of Z-1-halo-1-alkenyl-1,3,2-dioxaborolane has been developed as a convenient route to the synthesis of β,γ-unsaturated ketones.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(94)88199-5