Organic synthesis using haloboration reaction. Part 9. A direct and selective synthesis of (Z,Z)-1-bromo-1,3-dienes and (E,Z)-1,3-dienes by the hydroboration-bromoboration sequence of two alkynes
作者:Satoshi Hyuga、Satoru Takinami、Shoji Hara、Akira Suzuki
DOI:10.1016/s0040-4039(00)84153-2
日期:1986.1
1-Alkenyldibromoboranes readily obtainable by the hydroboration of first alkynes with dibromoborane-dimethyl sulfide followed by treatment with tribromoborane, react without any difficulty with second 1-alkynes as bromoborating agents to give (1-a1keny1)(2-bromo-1-alkeny)- bromoboranes (5). The reaction of 5 with iodine in the presence of potassium acetate provides (Z,Z)-1-bromo-1,3-dienes (6), specifically
通过先将二炔与二溴硼烷-二甲基硫醚加氢硼化,然后用三溴硼烷处理,即可轻松制得1-烯基二溴硼烷,与作为溴化硼剂的第二个1-炔烃毫不费力地反应,即可制得(1-a1keny1)(2-bromo-1-alkeny) -溴硼烷(5)。5在乙酸钾存在下与碘的反应提供了(Z,Z)-1-溴-1,3-二烯(6),具体而言,它们很容易转化为相应的(E,Z)-1,3 -用二叔丁基锂和甲醇处理二烯二烯(7)。