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Synfacts 2009(3): 0320-0320
DOI: 10.1055/s-0028-1087708
DOI: 10.1055/s-0028-1087708
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Alkenylboronates via Hydrocupration/Transmetalation
B. H. Lipshutz*, Ž V. Boškovič, D. H. Aue*
University of California, Santa Barbara, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Februar 2009 (online)
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.