I am trying to understand the stereochemistry of iodolactonisation of this cyclohexene. I can't work out if the iodonium ion would form on top or the bottom.
There is $\ce{CH2COO-}$ and $\ce{Me}$ pointing up, and $\ce{CH2OTBS}$ and $\ce{Me}$ pointing down. My guess would be iodine attacks from the top because there is a bulky $\ce{TBS}$ group pointing down as well as a methyl, however there is a semi-big $\ce{CH2COO-}$ group pointing up right next to the double bond. Would that have more of an effect as it is nearer to the double bond?