Asymmetric Synthesis of a Potent CXCR7 Modulator Featuring a Hindered Tertiary β-Amino Amide Stereocenter
A practical and asymmetric synthesis of a small-molecule CXCR7 modulator featuring a highly functionalized and hindered tertiary β-amino amide framework is reported. The cornerstone of this strategy relied on the intermediacy of a reactive aziridinium species, which, following regioselective ring opening with cyanide, furnished the desired chiral β-tertiary amino nitrile for further elaboration. As a means of further highlighting this synthetic strategy, an expanded scope of hindered β-amino amide synthesis is also presented.