To explore a wider range of substrates, multicomponent reaction (MCR) conditions previously used to generate N-Cbz imines from chiral aldehydes in situ were optimized for reactions using N-Ts imines (Table ). These conditions avoid the requisite precipitation of the amido-sulfone intermediates, which is strongly substrate-dependent and does not consistently produce a solid, preventing isolation. Observed diastereomeric ratios using MCR conditions and Cu(OTf)2 matched with the diastereomeric ratios using amidosulfone derived imines and the same Lewis acid (Table , entry 6). Unlike the other Lewis acids used under MCR conditions, Cu(OTf)2 preferentially mediated addition to the imine rather than the aldehyde and resulted in no detectable aldehyde addition product. However, reactions using Cu(OTf)2 led to no observed product in the presence of proton scavenger 2,6-ditert-butylpyridine (Table , entry 12). This observation accompanied by the analogous experiment performed on isolated imine 12 (see Table , entry 14) led to the conclusion that the reaction with Cu(OTf)2 likely proceeds through formation of an iminium ion and observed diastereomeric ratios result from intramolecular hydrogen bonding, or protonchelation. Previous reports also corroborate proton-chelation in the case of N-Cbz and N-Ts imines. With optimized MCR conditions, aldehydes 20a-20h were converted to allylated products 21a-21h using MCR conditions B (Table ). Diastereomeric ratios trended upwards with steric bulk at the R 1 position. Employment of tert-butyl-diphenylsilyl (TBDPS) group at R 2 resulted in complete erosion of selectivity for the reaction (Table , entry 1). Sterically hindered silylether substituents have less binding affinity for Lewis acids, disfavoring chelate formation. Aldehyde 19g produced an equal mixture of diastereomeric products, presumably due to bearing methyl substituents on both sides of the preformed chelate (Table , entry 7). Allylation of 19h resulted in major diastereomer anti-20h in 67:33 ratio (Table , entry 8), despite compounded steric bulk to one side of the chelate.