Synfacts 2015; 11(1): 0073
DOI: 10.1055/s-0034-1379656
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

An Efficient, Practical, and Selective Multicomponent Copper-Catalyzed Process

Contributor(s):
Paul Knochel
,
Thomas Klatt
Meng F, McGrath KP, Hoveyda AH * Boston College, Chestnut Hill, USA
Multifunctional Organoboron Compounds for Scalable Natural Product Synthesis.

Nature 2014;
513: 367-374
Further Information

Publication History

Publication Date:
15 December 2014 (online)

 

Significance

The authors demonstrate the generation of multifunctional alkenylboron fragments starting from two simple unsaturated organic molecules and a commercially available diboron reagent. These fragments were shown to carry several advantageous properties. The catalyst used is generated in situ by the reaction of inexpensive CuCl with a chiral ligand which was prepared on multigram scale in good yield.


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Comment

The practical protocol can be performed on large scale and makes gram quantities of a variety of complex organic molecules easily available. The products, which contain a stereogenic carbon center, a monosubstituted alkene, and an easily functionalizable Z-trisubstituted alkenylboron group, are obtained in good yields and excellent selectivities.


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