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Synfacts 2010(3): 0331-0331  
DOI: 10.1055/s-0029-1219317
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Vicinal Diboronates by Cu(I)-Catalyzed B-Cu Addition to Alkynes

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
Y. Lee, H. Jang, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The authors have developed a c­opper-N-heterocyclic carbene (NHC) catalyzed diboronation of terminal alkynes. The resulting vicinal diboronates were obtained in high yields and excellent enantioselectivities. Mechanistic studies revealed that this high regio- and stereoselectivity is due to the bidentate property of ligand 1. All the monodentate ligands 2-4, which do not have the second sulfonate moiety, gave the products with poor yield and poor regio- and stereoselectivities.