Skip to main content
. Author manuscript; available in PMC: 2019 Aug 22.
Published in final edited form as: J Am Chem Soc. 2018 Aug 10;140(33):10593–10601. doi: 10.1021/jacs.8b06699

Figure 5. Synthesis of chiral α-substituted amines.

Figure 5.

(a) As demonstrated through preparation of β-amino amide 3u-(R), the catalytic reactions are amenable to gram-scale operations. (b) The versatility of 3u-(R) was demonstrated by its conversion into a β-amino ester, a β-amino alcohol and a β-amino acid. The absolute configuration of 3u-(R) was determined by X-ray crystallographic analysis of 5d. (c) A series of N-alkylamines reacted with 2 to afford the corresponding β-amino amides. For 3v and 4f–4h, diastereomers were isolated by silica gel chromatography and then converted into β-amino esters (5) that were determined to be enantiomerically pure.