For example, a [2+1] cycloaddition involves a 3-membered ring transition state where two atoms of the ring come from the alkene substrate (HOMO, nucleophile) and one atom of the ring comes from the el...For example, a [2+1] cycloaddition involves a 3-membered ring transition state where two atoms of the ring come from the alkene substrate (HOMO, nucleophile) and one atom of the ring comes from the electrophile. Because of the 5-membered ring transition state, the delivery of the two alcohol functional groups occurs from the same face of the alkene.