The minimal enantioinduction afforded by the free methylene and terminal olefin of 3f (4f, 48:52 er) highlights that a fully substituted center adjacent to the olefin is necessary for significant enantioselectivity. We observe slightly increased net enantioinduction when comparing the dimethyl-substituted thiazolidine (4d; 61:39 er) to the slightly bulkier spirocyclohexane (4g; 37.5:62.5 er). Similarly, 4e gave a lower er than 4h. The most significant variable is the steric bulk from an internal olefin, evidenced by 3e (4e, 25:75 er) and 3h (4h, 80:20 er) exhibiting the highest enantioselectivity of all the tested substrates. Unfortunately, these bulky substrates also provided the lowest yields, and additional optimization would be required to increase the synthetic utility in these cases. Overall, the enantioinduction is influenced strongly by steric effects for this hydrogenation system.