Novel Diastereoselective Synthesis of (E)- and (Z)-Allylsilanes via Organoboranes

Autor:	Narayan G. Bhat, Wendy C. Lai, Matthew B. Carroll
Rok vydání:	2007
Předmět:	chemistry.chemical_classification Sulfide Organic Chemistry Diol chemistry.chemical_element General Medicine Iodine Biochemistry Medicinal chemistry Hydroboration chemistry.chemical_compound chemistry Drug Discovery Organic chemistry Methanol Spectral data
Zdroj:	ChemInform. 38
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200739161
Popis:	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).
Databáze:	OpenAIRE
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