期刊
ORGANIC LETTERS
卷 11, 期 18, 页码 4092-4095出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol901566e
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资金
- National Institutes of Health [GM 36792]
- Purdue University
- Sigma-Aldrich
- Albemarle
- Boulder Scientific
Contrary to all previous reports, bromoboration of propyne with BBr3 proceeds in >= 98% syn-selectivity to produce (Z)-2-bromo-1-propenyldibromoborane (1). Although 1 is readily prone to stereoisomerization, it can be converted to the pinacolboronate (2) of >= 98% isomeric purity by treatment with pinacol, which may then be subjected to Negishi coupling to give trisubstituted (Z)-alkenylpinacolboronates (3) containing various R groups in 73-90% yields. Iodinolysis of 3 affords alkenyl iodides (4) in 80-90% yields. All alkenes isolated and identified are >= 98% Z
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