To further illustrate the utility of the enantioenriched α-hydroxy amides 2, follow-up transformations were investigated (Scheme 4). For instance, reduction of the amide functionality of 2a with LiAlH4 to the corresponding β-amino alcohol 3 occurred without racemization. An inversion of the hydroxyl stereogenic center achieved by a Mitsunobu reaction with phenol as the nucleophile (4). A two-step procedure involving mesylation and azidation converted the hydroxyl group of 2a into the corresponding azide 5 with inversion of configuration. Moreover, the present method was used for the synthesis of potent brain penetrant adaptor protein 2-associated kinase 1 (AAK1) inhibitor 9 (IC50=12 nM), which is of potential use for the treatment of neuropathic pain. [22] The required (S)-N-sulfinyl acrylamide Taken together with data on DAP catalysis, these findings contribute to the proposition of the following mechanism and catalytic cycle (Scheme 6). First, DAP-OBn pre-catalyst is converted to the active DAP-H species I by σ-bond metathesis with pinacolborane. In turn, hydride I engages in a conjugate addition across acryl amide 1 leading to phosphinyl enol ether II.