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Synfacts 2010(1): 0063-0063  
DOI: 10.1055/s-0029-1218507
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of 2-Methyl-3-butene-1,2-diols

Contributor(s): Hisashi Yamamoto, Zhi Li
M. Chen, M. Handa, W. R. Roush*
Scripps Florida, Jupiter, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

A new stereoselective synthesis of both syn and anti isomers of 2-methyl-3-butene-1,2-diols was developed. 1-Methylallenylborate hydroboration at room temperature generates kinetic intermediate (Z)-allylborane. It isomerizes to the thermodynamically more stable (E)-isomer at 85 ˚C. The following aldehyde allylboration generates target diols in good yields and stereoselectivities.