Chiral vicinal aminoalcohols are ubiquitous in nature and represent a critical class of biologically active compounds for applications in medicine and the pharmaceutical industry. Consequently, asymmetric synthetic methods for the efficient preparation of the 1,2-aminoalcohol motif are needed to produce these valuable compounds. The dissonant nature of 1,2-aminoalcohols make them difficult to access through traditional two-electron chemistry. We have studied Cu-catalyzed reductive coupling reactions between allenamides and carbonyl compounds as a useful umpolung approach to generate vicinal aminoalcohols in high levels of regio-, diastereo-, and enantioselectivity. Being a cheap and abundant metal, these Cu-catalyzed process allow for the green, cost-effective, safe, scalable, and sustainable synthesis of 1,2-aminoalcohols. The development of these asymmetric processes for the synthesis of 1,2-aminoalcohols will be presented.

Synthesis Of 1,2-aminoalcohols through enantioselective aminoallylation of carbonyls via Cu-catalyzed reductive coupling

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