Asymmetric suprafacial 1,3-migration

If we do the same analysis for the 1,5-hydride shift, however, all is well (Figure 18.38). Some examples of 1,5-hydride shifts are shown in Figure 18.39. Notice in the second example that the chirality at the original asymmetric carbon atom is fully transferred to the new chiral carbon, by the suprafacial migration. 

If the reaction requires a suprafacial rearrangement, carbon will migrate using one of its lobes if the HOMO is symmetric and will migrate using both of its lobes if the HOMO is asymmetric. 

---