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Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes. A short access to polyenaldehydes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
39
Identifiers
DOI: 10.1016/s0040-4039(98)01544-5

Abstract

Abstract The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a γ-specific reaction occurs. According to the reaction conditions a γ; 1,2 or a γ; 1,4 coupled product was selectively obtained with enals. The γ; 1,2 reaction provided an efficient prenylation procedure. A short two-step synthesis of retinal is described.

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