Abstract Intramolecular allylboration reaction of 7-oxo-2-heptenyl boronates leads to 2- vinylcyclopentanols. The cyclization proceeds in a stereospecific manner, such that the (E)- allylboronate 8 is converted into trans-2-vinylcyclopentanol (2) and the (Z)-allylboronate 10 into cis-2-vinylcyclopentanol (3). Asymmetric induction originating from stereogenic centers placed between the boronate and the aldehyde function has been found to be low.