Synthesis of Z-alkenes from alkenylcatecholboranes through reaction with RMgX and I2 induced rearrangement

Article abstract of DOI:10.1016/0040-4020(95)00023-2

Addition of RMgX and BrMg(CH₂)nMgBr reagents to alkenylcatecholborane followed by iodine induced rearrangement and oxidation provided Z-olefins and Z-olefinic alcohols in moderate to good yields. This procedure is advantageous over the previous methods of synthesis of Z-olefins from alkenylboranes since the alkyl groups which are not available through hydroborations can also be utilized.