A simple, novel diastereoselective synthesis of both (E)- and (Z)-allylsilanes via organoboranes is developed. (E)-1-Alkenylboronate esters easily prepared from the corresponding terminal alkynes via hydroboration with dibromoborane-methyl sulfide complex followed by treatment with 1,3-propane diol readily react with trimethylsilylmethyllithium at -78 °C in methanol followed by reaction with iodine in methanol to produce the corresponding (Z)-allylsilanes in high yields (72-80%) and in high stereochemical purities (98% as evidenced by CMR spectral data). Similarly, the (Z)-1-alkenylboronate esters react with trimethylsilylmethyllithium at -78 °C in methanol followed by treatment with iodine in methanol to produce the corresponding (E)-allylsilanes in moderate yields (57-65%) in high stereochemical purities (>98% as revealed by CMR spectral data). © 2007 Elsevier Ltd. All rights reserved.
CITATION STYLE
Bhat, N. G., Lai, W. C., & Carroll, M. B. (2007). Novel diastereoselective synthesis of (E)- and (Z)-allylsilanes via organoboranes. Tetrahedron Letters, 48(24), 4267–4269. https://doi.org/10.1016/j.tetlet.2007.04.052
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