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Synfacts 2009(3): 0320-0320  
DOI: 10.1055/s-0028-1087708
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Alkenylboronates via Hydrocupration/Transmetalation

Contributor(s): Paul Knochel, Tobias Thaler
B. H. Lipshutz*, Ž V. Boškovič, D. H. Aue*
University of California, Santa Barbara, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

A novel stereoselective synthesis of vinylboronates bearing an activating alkoxycarbonyl substituent in the α-position has been described. Catalytic 1,2-addition of ”CuH" to acetylenic esters and immediate transmetalation with pinacolboranes provides the syn-hydroboration products with good to excellent yields and dia­stereoselectivities.