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Synfacts 2010(1): 0053-0053  
DOI: 10.1055/s-0029-1218483
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

cis-Selective Hydroboration of Allenes

Contributor(s): Mark Lautens, Jane Panteleev
J. Kister, A. C. DeBaillie, R. Lira, W. R. Roush*
Scripps Florida, Jupiter, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

The authors report a hydroboration of allenes giving Z-alkenes. Subsequent allylboration can be carried out in high diastereo- and enantioselectivity. Access to these alkenes through hydroboration is difficult because of competing isomerization to the thermodynamically favored E-alkenes. The use of the Soderquist borane 2 is noteworthy (J. A. Soderquist and co-workers J. Am. Chem. Soc. 2008, 130, 9218).

Review: For a review on allylboration, see: D. G. Hall Pure Appl. Chem. 2008, 80, 913-927.