Title of article :
Novel diastereoselective synthesis of (E)- and (Z)-allylsilanes via organoboranes
Bhat، نويسنده , , Narayan G. and Lai، نويسنده , , Wendy C. and Carroll، نويسنده , , Matthew B.، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2007
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).
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