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Synfacts 2014; 10(1): 0074
DOI: 10.1055/s-0033-1340363
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Highly α-Regioselective 1,4-Addition of Chalcones with Prenyl Bromide

Contributor(s):
Paul Knochel
,
Christoph Sämann
Zhao L.-M, * Zhang S.-Q, Dou F, Sun R. Jiangsu Normal University, Xuzhou, P. R. of China
Zinc-Mediated Highly α-Regioselective 1,4-Addition of Chalcones with Prenyl Bromide in THF.

Org. Lett. 2013;
15: 5154-5157
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

chalcones - α-regioselective 1,4-addition - zinc

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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