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Synfacts 2014; 10(1): 0074
DOI: 10.1055/s-0033-1340363
DOI: 10.1055/s-0033-1340363
Metal-Mediated Synthesis
Highly α-Regioselective 1,4-Addition of Chalcones with Prenyl Bromide
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
13. Dezember 2013 (online)
Significance
An efficient method for the introduction of a prenyl group onto the β-position of chalcones by zinc-mediated conjugate addition in the presence of tin(IV) chloride (SnCl4) is reported. The corresponding products are obtained in high yields and excellent α/γ-selectivities.
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Comment
The reaction has proven to be highly α-regioselective in a 1,4-manner. Moreover, the α-regioselectivity of these additions is higher than that of the corresponding addition of allylic barium, lithium, and copper reagents.
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