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Synfacts 2010(8): 0903-0903  
DOI: 10.1055/s-0030-1257782
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

E-Selective Allylboration of α-Substituted Allylboronates

Contributor(s): Mark Lautens, Jane Panteleev
M. Chen, W. R. Roush*
Scripps Florida, Jupiter, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

An example of a highly E-selective allylboration of α-substituted allylboronates is presented. This work is closely related to an earlier report by D. G. Hall (J. Am. Chem. Soc. 2007, 129, 3070) wherein allylboration of α-methylene TMS substituted substrates was explored. This work is noteworthy since earlier reports of similar reactions give low selectivity for α-methylated boro­nates. Notably, even α-chloroallylboronate gives the E-product under the reported conditions; contrary to earlier observations. As commonly seen in these reactions, the chirality transfer from allylboronates to the alcohol is excellent.

Review: S. E. Denmark, J. Fu. Chem. Rev. 2003, 103, 2763-2793.