Important biologically active organic compounds such as natural products and pharmaceuticals often contain multiple oxygen and nitrogen heteroatoms within their carbon framework. Furthermore, chiral 1,2-aminoalcohol substitution patterns are often present in such compounds. As a result, efficient methods to access the 1,2-aminoalcohol motif while installing additional functionality for subsequent diversification in a stereoselective manner is highly desirable. Towards this end, we report a strategy based on Cu-catalyzed enantioselective borylative aminoallylation of aldehydes using a N-substituted allene to access boryl-substituted 1,2-aminoalcohol synthons for diversification to chiral heteroatom-rich organic compounds. The reported reaction provides access to several different substitution patterns of chiral 1,2-aminoalcohol products from the same readily available starting materials with high enantioselectivity (>95:5 er).