With the development of a high yielding reaction mediated by fully achiral components, we began to test the feasibility of asymmetric hydrogenation with a commercially available chiral thiol: a thioglycoside utilized by Roberts and coworkers (C1). 18a, The current conditions (Table , entry 1) afforded a high yield but minimal enantioinduction. A number of variations led to alteration of the reaction efficiency but no enhanced enantioselectivity. For example, moderate heating to 50 °C led to lower yield and nearly racemic product (Table , entry 2). The reasons for this decreased yield and enantioselectivity at increased temperature may be many, including accelerated decomposition of the iron catalyst, the silane reductant, or both. This hypothesis is supported by the observation of significant trialkoxysilane formation in the reaction by GC-FID and GC-MS, which is consistent with decomposition of silane. Changing the EtOH solvent to iPrOH similarly decreased reaction efficiency (Table 2, entry 3), while no product formation was observed in TFE or HFIP (Table , entries 4-5).