To conclude, we have developed two optimized allylation reaction conditions for access to anti-1,3 amino alcohols either from β-alkoxy imine or aldehyde starting materials. Experimental and computational results show that Cu(OTf)2 mediated allylations of β-alkoxy imines are preceded by formation of a proton-chelate that can adopt two half-chair-like conformations. The observed diastereoselectivity of addition to the chelate is influenced by stereoelectronic interactions between half-chair chelates and nucleophile, as well as the conformational preferences of the chelate itself. The stereoelectronic considerations described herein resemble that of Fürst-Plattner rules and have been previously proposed to rationalize stereochemical outcomes of addition to tetrahydropyridinium ions. Together, we have proposed a generalizable stereoelectronic model describing nucleophilic additions to β-alkoxy imines, which will inform retrosynthetic planning of stereochemically-complex nitrogen-containing targets.